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139756-22-2

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  • 5-(5-Chlorosulfonyl-2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one/ LIDE PHARMA- Factory supply / Best price

    Cas No: 139756-22-2

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139756-22-2 Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 139756-22-2 differently. You can refer to the following data:
1. Sildenafil derivative
2. Sildenafil derivative.

Check Digit Verification of cas no

The CAS Registry Mumber 139756-22-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,9,7,5 and 6 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 139756-22:
(8*1)+(7*3)+(6*9)+(5*7)+(4*5)+(3*6)+(2*2)+(1*2)=162
162 % 10 = 2
So 139756-22-2 is a valid CAS Registry Number.
InChI:InChI=1/C17H19ClN4O4S/c1-4-6-12-14-15(22(3)21-12)17(23)20-16(19-14)11-9-10(27(18,24)25)7-8-13(11)26-5-2/h7-9H,4-6H2,1-3H3,(H,19,20,23)

139756-22-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzene-1-sulfonyl chloride

1.2 Other means of identification

Product number -
Other names 4-ethoxy-3-(1-methyl-7-oxo-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonyl chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:139756-22-2 SDS

139756-22-2Synthetic route

5-(2-ethoxy)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one
139756-21-1

5-(2-ethoxy)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
With chlorosulfonic acid at 0 - 25℃; for 2h;97%
With chlorosulfonic acid In neat (no solvent) at 0 - 20℃; for 12h;95%
With chlorosulfonic acid; thionyl chloride at 0 - 20℃; Sealed tube;92%
ethyl 3-butyrylpyruvate
36983-31-0

ethyl 3-butyrylpyruvate

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: hydrazine hydrate / acetic acid; 2-methoxy-ethanol / 100 °C
2: caesium carbonate / N,N-dimethyl-formamide / 20 °C
3: hydrogenchloride / water / 100 °C
4: nitric acid; sulfuric acid / 50 °C
5: thionyl chloride / Reflux
6: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
7: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
8: triethylamine / dichloromethane / 20 °C
9: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
10: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 10 steps
1: acetic acid; hydrazine hydrate / 2-methoxy-ethanol / 100 °C
2: caesium carbonate / N,N-dimethyl-formamide / 20 °C
3: hydrogenchloride; water / 100 °C
4: sulfuric acid; nitric acid / 50 °C
5: thionyl chloride / Reflux
6: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
7: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
8: triethylamine / dichloromethane / 20 °C
9: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
10: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
2-Pentanone
107-87-9

2-Pentanone

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: sodium / ethanol / 1 h / 20 °C
1.2: 20 °C
2.1: hydrazine hydrate / acetic acid; 2-methoxy-ethanol / 100 °C
3.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C
4.1: hydrogenchloride / water / 100 °C
5.1: nitric acid; sulfuric acid / 50 °C
6.1: thionyl chloride / Reflux
7.1: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
8.1: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
9.1: triethylamine / dichloromethane / 20 °C
10.1: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
11.1: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 11 steps
1.1: sodium / ethanol / 1 h / 20 °C
1.2: 20 °C
2.1: acetic acid; hydrazine hydrate / 2-methoxy-ethanol / 100 °C
3.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C
4.1: hydrogenchloride; water / 100 °C
5.1: sulfuric acid; nitric acid / 50 °C
6.1: thionyl chloride / Reflux
7.1: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
8.1: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
9.1: triethylamine / dichloromethane / 20 °C
10.1: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
11.1: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
ethyl 3-propyl-1H-pyrazole-5-carboxylate
92945-27-2

ethyl 3-propyl-1H-pyrazole-5-carboxylate

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: caesium carbonate / N,N-dimethyl-formamide / 20 °C
2: hydrogenchloride / water / 100 °C
3: nitric acid; sulfuric acid / 50 °C
4: thionyl chloride / Reflux
5: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
6: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
7: triethylamine / dichloromethane / 20 °C
8: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
9: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 7 steps
1.1: 9 h / 5 - 25 °C
2.1: sodium hydroxide / 3 h / 75 °C
3.1: sulfuric acid; nitric acid / 8 h / 50 °C
4.1: thionyl chloride / 5 h / Reflux
5.1: iron; ammonium chloride / ethanol; water / 4.5 h / 80 °C
6.1: ethanol / 1.5 h / 70 °C
6.2: 1.5 h / 70 °C
7.1: chlorosulfonic acid / 0 - 5 °C
View Scheme
Multi-step reaction with 9 steps
1: caesium carbonate / N,N-dimethyl-formamide / 20 °C
2: hydrogenchloride; water / 100 °C
3: sulfuric acid; nitric acid / 50 °C
4: thionyl chloride / Reflux
5: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
6: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
7: triethylamine / dichloromethane / 20 °C
8: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
9: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
1-Methyl-3-n-propylpyrazole-5-carboxylic acid ethyl ester
133261-07-1

1-Methyl-3-n-propylpyrazole-5-carboxylic acid ethyl ester

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: hydrogenchloride / water / 100 °C
2: nitric acid; sulfuric acid / 50 °C
3: thionyl chloride / Reflux
4: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
5: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
6: triethylamine / dichloromethane / 20 °C
7: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
8: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydroxide / 3 h / 75 °C
2.1: sulfuric acid; nitric acid / 8 h / 50 °C
3.1: thionyl chloride / 5 h / Reflux
4.1: iron; ammonium chloride / ethanol; water / 4.5 h / 80 °C
5.1: ethanol / 1.5 h / 70 °C
5.2: 1.5 h / 70 °C
6.1: chlorosulfonic acid / 0 - 5 °C
View Scheme
Multi-step reaction with 8 steps
1: hydrogenchloride; water / 100 °C
2: sulfuric acid; nitric acid / 50 °C
3: thionyl chloride / Reflux
4: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
5: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
6: triethylamine / dichloromethane / 20 °C
7: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
8: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
1-methyl-3-propyl-1 H-pyrazole-5-carboxylic acid
139755-99-0

1-methyl-3-propyl-1 H-pyrazole-5-carboxylic acid

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: nitric acid; sulfuric acid / 50 °C
2: thionyl chloride / Reflux
3: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
4: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
5: triethylamine / dichloromethane / 20 °C
6: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
7: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 5 steps
1.1: sulfuric acid; nitric acid / 8 h / 50 °C
2.1: thionyl chloride / 5 h / Reflux
3.1: iron; ammonium chloride / ethanol; water / 4.5 h / 80 °C
4.1: ethanol / 1.5 h / 70 °C
4.2: 1.5 h / 70 °C
5.1: chlorosulfonic acid / 0 - 5 °C
View Scheme
Multi-step reaction with 7 steps
1: sulfuric acid; nitric acid / 50 °C
2: thionyl chloride / Reflux
3: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
4: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
5: triethylamine / dichloromethane / 20 °C
6: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
7: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
1-methyl-2-nitro-3-propyl-1H-pyrazole-5-carboxylic acid
139756-00-6

1-methyl-2-nitro-3-propyl-1H-pyrazole-5-carboxylic acid

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: thionyl chloride / Reflux
2: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
3: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
4: triethylamine / dichloromethane / 20 °C
5: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
6: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 4 steps
1.1: thionyl chloride / 5 h / Reflux
2.1: iron; ammonium chloride / ethanol; water / 4.5 h / 80 °C
3.1: ethanol / 1.5 h / 70 °C
3.2: 1.5 h / 70 °C
4.1: chlorosulfonic acid / 0 - 5 °C
View Scheme
Multi-step reaction with 6 steps
1: thionyl chloride / Reflux
2: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
3: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
4: triethylamine / dichloromethane / 20 °C
5: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
6: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
1-methyl-4-nitro-3-propyl-1H-pyrazole-5 carboxamide
139756-01-7

1-methyl-4-nitro-3-propyl-1H-pyrazole-5 carboxamide

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
2: triethylamine / dichloromethane / 20 °C
3: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
4: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 3 steps
1.1: iron; ammonium chloride / ethanol; water / 4.5 h / 80 °C
2.1: ethanol / 1.5 h / 70 °C
2.2: 1.5 h / 70 °C
3.1: chlorosulfonic acid / 0 - 5 °C
View Scheme
Multi-step reaction with 4 steps
1: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
2: triethylamine / dichloromethane / 20 °C
3: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
4: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
1-methyl-4-nitro-3-propyl-1H-pyrazole-5-carbonyl chloride
360068-47-9

1-methyl-4-nitro-3-propyl-1H-pyrazole-5-carbonyl chloride

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
2: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
3: triethylamine / dichloromethane / 20 °C
4: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
5: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 5 steps
1: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
2: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
3: triethylamine / dichloromethane / 20 °C
4: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
5: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide
139756-02-8

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 20 °C
2: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
3: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1.1: ethanol / 1.5 h / 70 °C
1.2: 1.5 h / 70 °C
2.1: chlorosulfonic acid / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 20 °C
2: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
3: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
5-(2-ethoxyphenylcarbonylaminocarbonyl)-1-methyl-3-propyl-1H-pyrazol-4-amine

5-(2-ethoxyphenylcarbonylaminocarbonyl)-1-methyl-3-propyl-1H-pyrazol-4-amine

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
2: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
2: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
C10H9O4(1-)*K(1+)

C10H9O4(1-)*K(1+)

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dipotassium peroxodisulfate / acetonitrile / 8 h / 80 °C / Sealed tube; Inert atmosphere
2: chlorosulfonic acid / 0 - 20 °C / Sealed tube
View Scheme
2-ethoxylbenzaldehyde
613-69-4

2-ethoxylbenzaldehyde

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol / 1.5 h / 70 °C
2: copper dichloride; oxygen / ethanol / 1.5 h / 70 °C
3: chlorosulfonic acid / 0 - 5 °C
View Scheme
C17H22N4O2
845302-49-0

C17H22N4O2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper dichloride; oxygen / ethanol / 1.5 h / 70 °C
2: chlorosulfonic acid / 0 - 5 °C
View Scheme
2-ethoxybenzoyl chloride
42926-52-3

2-ethoxybenzoyl chloride

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 1.5 h / 20 °C
2: sodium hydroxide / tert-butyl alcohol / 35 h / 80 - 90 °C
3: chlorosulfonic acid / 12 h / 20 - 30 °C
View Scheme
4-[(2-ethoxybenzoyl)amino]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide
139756-03-9

4-[(2-ethoxybenzoyl)amino]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / tert-butyl alcohol / 35 h / 80 - 90 °C
2: chlorosulfonic acid / 12 h / 20 - 30 °C
View Scheme
4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonic acid
1357931-55-5

4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonic acid

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0℃; for 5h; Inert atmosphere;
viagra
139755-83-2

viagra

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid; water / 41 h / 20 - 100 °C
2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 5 h / 0 °C / Inert atmosphere
View Scheme
2-(2-ethoxyphenyl)acetic acid
70289-12-2

2-(2-ethoxyphenyl)acetic acid

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dipotassium peroxodisulfate / water / 12 h / 80 °C / Sealed tube
2: chlorosulfonic acid; thionyl chloride / 0 - 20 °C / Sealed tube
View Scheme
2-Hydroxyphenylacetic acid
614-75-5

2-Hydroxyphenylacetic acid

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetonitrile / 4 h / 80 °C / Sealed tube
2: dipotassium peroxodisulfate / water / 12 h / 80 °C / Sealed tube
3: chlorosulfonic acid; thionyl chloride / 0 - 20 °C / Sealed tube
View Scheme
1,4-Diazacycloheptane
505-66-8

1,4-Diazacycloheptane

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

5-(5-(1,4-diazepane-1-ylsulfonyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one
1352238-20-0

5-(5-(1,4-diazepane-1-ylsulfonyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
With triethylamine In ethanol at 0 - 10℃; for 1h; Concentration; Inert atmosphere;98%
1-Methylhomopiperazine
4318-37-0

1-Methylhomopiperazine

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

5-[2-ethoxy-5-(4-methyl-1-homopiperazinylsulfonyl)]-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d]pyrimidine-7-one
1257393-31-9

5-[2-ethoxy-5-(4-methyl-1-homopiperazinylsulfonyl)]-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d]pyrimidine-7-one

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 1h; Concentration; Solvent; Inert atmosphere;97.5%
With N-ethyl-N,N-diisopropylamine In chloroform for 12h; pH=9; Cooling with ice;92.2%
With N-ethyl-N,N-diisopropylamine In chloroform for 12h; pH=9; Cooling with ice;92.2%
2-Ketopiperazine
5625-67-2

2-Ketopiperazine

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

5-(2-ethoxy-5-((3-oxopiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

5-(2-ethoxy-5-((3-oxopiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
Stage #1: 2-Ketopiperazine With triethylamine In chloroform at 10℃; for 0.166667h;
Stage #2: 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one In chloroform at 25℃; for 6h;
95%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃;70%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With pyridine In water at 50℃; Reagent/catalyst; Temperature;93.9%
With triethylamine In methanol at 20℃; for 0.75h; Product distribution / selectivity;91%
In acetone at 20℃; for 3h; Sealed tube;90%
piperazine
110-85-0

piperazine

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Desmethylsildenafil

Desmethylsildenafil

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h;93%
In ethanol at 100℃; for 1h; Microwave irradiation;87%
In ethanol at 100℃; for 1h; Microwave irradiation;86.8%
In ethanol at 100℃; for 1h; Microwave irradiation;86.8%
In ethanol at 20℃; for 3h;72.3%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

N-acetylhomopiperizine
61903-11-5

N-acetylhomopiperizine

5-(5-(4-acetyl-1,4-diazepan-1-ylsulfonyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one
1352238-21-1

5-(5-(4-acetyl-1,4-diazepan-1-ylsulfonyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 1h; Inert atmosphere;93%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

4-(piperazin-1-yl)pyridine
1008-91-9

4-(piperazin-1-yl)pyridine

5-(2-ethoxy-5-((4-(pyridin-4-yl)piperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

5-(2-ethoxy-5-((4-(pyridin-4-yl)piperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
Stage #1: 4-(piperazin-1-yl)pyridine With triethylamine In chloroform at 10℃; for 0.166667h;
Stage #2: 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one In chloroform at 25℃; for 6h;
93%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃;70%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

7-chloro-1-methyl-5-[2-ethoxy-5-(chlorosulfonyl)phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine
1033861-31-2

7-chloro-1-methyl-5-[2-ethoxy-5-(chlorosulfonyl)phenyl]-3-n-propyl-1H-pyrazolo[4,3-d]pyrimidine

Conditions
ConditionsYield
With trichlorophosphate at 70 - 80℃; for 2h; Product distribution / selectivity;92%
With trichlorophosphate at 80℃; for 2h; Product distribution / selectivity;92%
With phosphorus pentachloride In benzene at 0 - 90℃; for 2.5h; Product distribution / selectivity;67%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

N-(2-aminoethyl)benzeneamine
1664-40-0

N-(2-aminoethyl)benzeneamine

C25H30N6O4S
1007310-81-7

C25H30N6O4S

Conditions
ConditionsYield
With triethylamine In ethanol at 30℃; for 0.0833333h; microwave irradiation;92%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

N-(2-pyridinyl)piperazine
20980-22-7

N-(2-pyridinyl)piperazine

5-(2-ethoxy-5-((4-(pyrimidin-2-yl)piperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

5-(2-ethoxy-5-((4-(pyrimidin-2-yl)piperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
Stage #1: N-(2-pyridinyl)piperazine With trimethylamine In 1,4-dioxane at 15℃; for 0.166667h;
Stage #2: 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one In 1,4-dioxane at 27℃; for 6h;
92%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

azetion-3-ol hydrochloride
18621-18-6

azetion-3-ol hydrochloride

5-(2- ethoxy-5-((3-hydroxyazetidin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

5-(2- ethoxy-5-((3-hydroxyazetidin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 25℃; for 16h;91.81%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

1-methylpiperazine hydrochloride
34352-59-5, 50398-09-9, 51545-09-6

1-methylpiperazine hydrochloride

viagra
139755-83-2

viagra

Conditions
ConditionsYield
With triethylamine; N-ethyl-N,N-diisopropylamine In water at 60℃; for 1.2h;91.8%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

1-(2-pyridyl)piperazine
34803-66-2

1-(2-pyridyl)piperazine

5-(2-ethoxy-5-((4-(pyridin-2-yl)piperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

5-(2-ethoxy-5-((4-(pyridin-2-yl)piperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
Stage #1: 1-(2-pyridyl)piperazine With caesium carbonate In N,N-dimethyl-formamide at 15℃; for 0.166667h;
Stage #2: 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one In N,N-dimethyl-formamide at 35℃; for 4h;
91%
4-benzylpyperidine
31252-42-3

4-benzylpyperidine

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

5-(5-((4-benzylpiperidin-1-yl)sulfonyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

5-(5-((4-benzylpiperidin-1-yl)sulfonyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
Stage #1: 4-benzylpyperidine With triethylamine In dichloromethane at 20℃; for 0.166667h;
Stage #2: 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one In dichloromethane at 30℃; for 6h;
91%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃;70%
cyclohexylpiperazine
17766-28-8

cyclohexylpiperazine

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

C27H38N6O4S
1007310-71-5

C27H38N6O4S

Conditions
ConditionsYield
With triethylamine In ethanol at 30℃; for 0.0833333h; microwave irradiation;90%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

1-(o-toluyl)piperazine
39512-51-1

1-(o-toluyl)piperazine

C28H34N6O4S
1007310-64-6

C28H34N6O4S

Conditions
ConditionsYield
With triethylamine In ethanol at 30℃; for 0.0833333h; microwave irradiation;90%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

1-(2-Methoxyphenyl)piperazine
35386-24-4

1-(2-Methoxyphenyl)piperazine

C28H34N6O5S
1007310-58-8

C28H34N6O5S

Conditions
ConditionsYield
With triethylamine In ethanol at 30℃; for 0.0833333h; microwave irradiation;90%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

1-(4-Nitrophenyl)piperazine
6269-89-2

1-(4-Nitrophenyl)piperazine

C27H31N7O6S
1007310-66-8

C27H31N7O6S

Conditions
ConditionsYield
With triethylamine In ethanol at 30℃; for 0.0833333h; microwave irradiation;90%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

1-(o-fluorophenyl)piperazine
1011-15-0

1-(o-fluorophenyl)piperazine

C27H31FN6O4S
1007310-67-9

C27H31FN6O4S

Conditions
ConditionsYield
With triethylamine In ethanol at 30℃; for 0.0833333h; microwave irradiation;90%
piperidin-4-one
41661-47-6

piperidin-4-one

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

5-(2-ethoxy-5-((4-oxopiperidin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

5-(2-ethoxy-5-((4-oxopiperidin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
Stage #1: piperidin-4-one With N-ethyl-N,N-diisopropylamine In dichloromethane at 15℃; for 0.166667h;
Stage #2: 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one In dichloromethane at 25℃; for 6h;
90%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃; for 6h;90%
4-methoxypiperidine
4045-24-3

4-methoxypiperidine

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

5-(2-ethoxy-5-((4-methoxypiperidin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

5-(2-ethoxy-5-((4-methoxypiperidin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
Stage #1: 4-methoxypiperidine With potassium carbonate In acetone at 20℃; for 0.166667h;
Stage #2: 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one In acetone at 35℃; for 5h;
90%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃;80%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

4'-piperazinoacetophenone
51639-48-6

4'-piperazinoacetophenone

5-(5-((4-(4-acetylphenyl)piperazin-1-yl)sulfonyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

5-(5-((4-(4-acetylphenyl)piperazin-1-yl)sulfonyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
Stage #1: 4'-piperazinoacetophenone With potassium carbonate In acetonitrile at 20℃; for 0.166667h;
Stage #2: 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one In acetonitrile at 35℃; for 5h;
90%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃;65%
4-piperidinopiperidin
4897-50-1

4-piperidinopiperidin

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

5-(5-([1,4’-bipiperidin]-1‘-ylsulfonyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

5-(5-([1,4’-bipiperidin]-1‘-ylsulfonyl)-2-ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
Stage #1: 4-piperidinopiperidin With potassium carbonate In acetone at 25℃; for 0.166667h;
Stage #2: 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one In acetone at 25℃; for 4.5h;
90%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃;65%
4-methylpiperidin
626-58-4

4-methylpiperidin

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

5-(2-ethoxy-5-((4-methylpiperidin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

5-(2-ethoxy-5-((4-methylpiperidin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
Stage #1: 4-methylpiperidin With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 0.166667h;
Stage #2: 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one In 1,2-dichloro-ethane at 30℃; for 6h;
90%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃;80%
With triethylamine In chloroform
With triethylamine In chloroform
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

(piperidin-4-yl)carbamic acid tert-butyl ester
73874-95-0

(piperidin-4-yl)carbamic acid tert-butyl ester

tert-butyl (1-((4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)sulfonyl)piperidin-4-yl)carbamate

tert-butyl (1-((4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)sulfonyl)piperidin-4-yl)carbamate

Conditions
ConditionsYield
Stage #1: (piperidin-4-yl)carbamic acid tert-butyl ester With N-ethyl-N,N-diisopropylamine In dichloromethane at 15℃; for 0.166667h;
Stage #2: 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one In dichloromethane at 30℃; for 6h;
90%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃;75%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonic acid
1357931-55-5

4-ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonic acid

Conditions
ConditionsYield
With ethanol for 5h; Reagent/catalyst; Reflux;90%
5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

1-naphtylpiperazine
57536-86-4

1-naphtylpiperazine

C31H34N6O4S
1007310-60-2

C31H34N6O4S

Conditions
ConditionsYield
With triethylamine In ethanol at 30℃; for 0.0833333h; microwave irradiation;89%
4-HYDROXYPIPERIDINE
5382-16-1

4-HYDROXYPIPERIDINE

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

5-(2-ethoxy-5-((4-hydroxypiperidin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

5-(2-ethoxy-5-((4-hydroxypiperidin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Conditions
ConditionsYield
Stage #1: 4-HYDROXYPIPERIDINE With N-ethyl-N,N-diisopropylamine In dichloromethane at 15℃; for 0.166667h;
Stage #2: 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one In dichloromethane at 25℃; for 4h;
88%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 15 - 25℃;85%

139756-22-2Relevant articles and documents

Discovery of in Vivo Chemical Probes for Treating Alzheimer's Disease: Dual Phosphodiesterase 5 (PDE5) and Class i Histone Deacetylase Selective Inhibitors

Rabal, Obdulia,Sánchez-Arias, Juan A.,Cuadrado-Tejedor, Mar,De Miguel, Irene,Pérez-González, Marta,García-Barroso, Carolina,Ugarte, Ana,Estella-Hermoso De Mendoza, Ander,Sáez, Elena,Espelosin, Maria,Ursua, Susana,Haizhong, Tan,Wei, Wu,Musheng, Xu,Garcia-Osta, Ana,Oyarzabal, Julen

, p. 1765 - 1782 (2019)

In order to determine the contributions of histone deacetylase (HDAC) isoforms to the beneficial effects of dual phosphodiesterase 5 (PDE5) and pan-HDAC inhibitors on in vivo models of Alzheimer's disease (AD), we have designed, synthesized, and tested novel chemical probes with the desired target compound profile of PDE5 and class I HDAC selective inhibitors. Compared to previous hydroxamate-based series, these molecules exhibit longer residence times on HDACs. In this scenario, shorter or longer preincubation times may have a significant impact on the IC50 values of these compounds and therefore on their corresponding selectivity profiles on the different HDAC isoforms. On the other hand, different chemical series have been explored and, as expected, some pairwise comparisons show a clear impact of the scaffold on biological responses (e.g., 35a vs 40a). The lead identification process led to compound 29a, which shows an adequate ADME-Tox profile and in vivo target engagement (histone acetylation and cAMP/cGMP response element-binding (CREB) phosphorylation) in the central nervous system (CNS), suggesting that this compound represents an optimized chemical probe; thus, 29a has been assayed in a mouse model of AD (Tg2576).

α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water

Huang, Jian,Chen, Wei,Liang, Jiazhi,Yang, Qin,Fan, Yan,Chen, Mu-Wang,Peng, Yiyuan

, p. 14866 - 14882 (2021/10/25)

A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).

Method for preparing sildenafil citrate

-

Paragraph 0107-0123, (2020/05/30)

The invention discloses a method for preparing sildenafil citrate. The preparation method comprises the following steps: (a) adding a compound II into chlorosulfonic acid for a reaction to generate anintermediate III; (b) reacting the intermediate III with N-methyl piperazine to generate a crude sildenafil product; (c) recrystallizing the crude sildenafil product to obtain a pure sildenafil product; and (d) carrying out a salifying reaction on the pure sildenafil product to obtain sildenafil citrate. The method is beneficial for industrial production.

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