1533519-84-4

Basic information

• Product Name: 4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione
• Synonyms: 4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione;lesinurad int.4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione;4-(4-Cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol;Sodium 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate;4-(4-cyclopropylnaphthalen-1-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione;Lesinurad Impurity 21;4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione (for Lesinurad);4-(4-Cyclopropylnaphthalen-1-yl)-1H-1
• CAS NO: 1533519-84-4
• Molecular Formula: C₁₅H₁₃N₃S
• Molecular Weight: 267.34882
• EINECS: 1592732-453-0
• Mol File: 1533519-84-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 435.2±38.0 °C(Predicted)
• Appearance: /
• Density: 1.41±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 7.89±0.20(Predicted)
• CAS DataBase Reference: 4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione(1533519-84-4)
• EPA Substance Registry System: 4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione(1533519-84-4)

Safety Data

• Hazardous Substances Data: 1533519-84-4(Hazardous Substances Data)

Usage

Description

4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione is an organic compound characterized by its off-white powder form. It is a derivative of the 1,2,4-triazole family, featuring a cyclopropylnaphthalenyl group attached to the 4th position and a thione group at the 5th position. 4-(4-cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione is known for its potential applications in various fields due to its unique chemical structure and properties.

Uses

Used in Pharmaceutical Industry:
4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione is used as a reagent for the discovery of Lesinurad, a HEK293 cell-based inhibitor. Lesinurad is a medication used to treat hyperuricemia, a condition characterized by high levels of uric acid in the blood, which can lead to gout and kidney stones. The compound plays a crucial role in the development and synthesis of Lesinurad, contributing to its therapeutic effects and potential benefits for patients suffering from hyperuricemia.
Used in Chemical Research:
In addition to its application in the pharmaceutical industry, 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione may also be utilized in chemical research and development. Its unique structure and properties make it a valuable compound for exploring new chemical reactions, synthesis pathways, and potential applications in various fields, including materials science, agrochemistry, and environmental science.

Synthetic route

N-(4-cyclopropylnaphthalen-1-yl)-2-formylhydrazine-1-thiocarboxamide (1533519-86-6) → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
With water; sodium hydroxide In N,N-dimethyl-formamide at 30℃; for 16h; Solvent; Temperature; Reagent/catalyst;	90%
With potassium hydrogencarbonate In water; N,N-dimethyl-formamide at 90 - 140℃;

C12H8ClN3S + cyclopropylmagnesium bromide (23719-80-4) → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
In tetrahydrofuran for 2h;	89.89%

1-amino-4-cyclopropylnaphthalene (878671-94-4) → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 2: N,N-dimethyl-formamide / 50 - 55 °C 3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme
Multi-step reaction with 4 steps 1: toluene; water 2: potassium hydroxide 3: N,N-dimethyl-formamide / 50 - 55 °C 4: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme
Multi-step reaction with 3 steps 1.1: potassium carbonate / water; N,N-dimethyl-formamide / 3.5 h / 15 °C 1.2: 1 h / 0 °C 1.3: 2 h 2.1: ethyl acetate / 2 h / 60 °C 3.1: sodium hydroxide; water / N,N-dimethyl-formamide / 16 h / 30 °C View Scheme

1-Bromonaphthalene (90-11-9) → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
Multi-step reaction with 6 steps 1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran / 0 - 5 °C 2: nitric acid / 0 - 20 °C 3: palladium on activated charcoal; hydrogen 4: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 5: N,N-dimethyl-formamide / 50 - 55 °C 6: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme
Multi-step reaction with 6 steps 1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran / 0 - 5 °C 2: nitric acid / 0 - 20 °C 3: hydrazine hydrate / methanol / Reflux 4: potassium hydroxide / dichloromethane 5: N,N-dimethyl-formamide / 50 - 55 °C 6: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme
Multi-step reaction with 7 steps 1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran / 0 - 5 °C 2: nitric acid / 0 - 20 °C 3: palladium on activated charcoal; hydrogen 4: toluene; water 5: potassium hydroxide 6: N,N-dimethyl-formamide / 50 - 55 °C 7: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme

1-cyclopropyl-naphthalene (25033-19-6) → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: nitric acid / 0 - 20 °C 2: palladium on activated charcoal; hydrogen 3: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 4: N,N-dimethyl-formamide / 50 - 55 °C 5: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme
Multi-step reaction with 5 steps 1: nitric acid / 0 - 20 °C 2: hydrazine hydrate / methanol / Reflux 3: potassium hydroxide / dichloromethane 4: N,N-dimethyl-formamide / 50 - 55 °C 5: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme
Multi-step reaction with 6 steps 1: nitric acid / 0 - 20 °C 2: palladium on activated charcoal; hydrogen 3: toluene; water 4: potassium hydroxide 5: N,N-dimethyl-formamide / 50 - 55 °C 6: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme

1-cyclopropyl-4-nitronaphthalene (878671-93-3) → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: palladium on activated charcoal; hydrogen 2: water; 5,5-dimethyl-1,3-cyclohexadiene / 90 - 140 °C 3: N,N-dimethyl-formamide / 50 - 55 °C 4: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme
Multi-step reaction with 4 steps 1: hydrazine hydrate / methanol / Reflux 2: potassium hydroxide / dichloromethane 3: N,N-dimethyl-formamide / 50 - 55 °C 4: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme
Multi-step reaction with 5 steps 1: palladium on activated charcoal; hydrogen 2: toluene; water 3: potassium hydroxide 4: N,N-dimethyl-formamide / 50 - 55 °C 5: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme

1-amino-4-cyclopropylnaphthalene oxalate (1533519-87-7) → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide 2: N,N-dimethyl-formamide / 50 - 55 °C 3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme

(1-cyclopropylnaphthalen-4-yl)isothiocyanate (878671-95-5) → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 50 - 55 °C 2: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme
Multi-step reaction with 2 steps 1: ethyl acetate / 2 h / 60 °C 2: sodium hydroxide; water / N,N-dimethyl-formamide / 16 h / 30 °C View Scheme

1-amino-4-cyclopropylnaphthalene hydrochloride (1533519-92-4) → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium hydroxide / dichloromethane 2: N,N-dimethyl-formamide / 50 - 55 °C 3: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme

tert-butyl 4-cyclopropylnaphthalen-1-ylcarbamate (1533519-91-3) → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride / ethanol 2: potassium hydroxide / dichloromethane 3: N,N-dimethyl-formamide / 50 - 55 °C 4: potassium hydrogencarbonate / N,N-dimethyl-formamide; water / 90 - 140 °C View Scheme

4-Bromo-1-naphthylamine (2298-07-9) → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium phosphate; palladium diacetate / toluene; water / 3 h / 110 °C / Inert atmosphere 2.1: potassium carbonate / water; N,N-dimethyl-formamide / 3.5 h / 15 °C 2.2: 1 h / 0 °C 2.3: 2 h 3.1: ethyl acetate / 2 h / 60 °C 4.1: sodium hydroxide; water / N,N-dimethyl-formamide / 16 h / 30 °C View Scheme

C12H9N3OS → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / dichloromethane / 4 h / Reflux 2: tetrahydrofuran / 2 h View Scheme

4-bromo-1-naphthol (571-57-3) → 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol / 3 h / 30 °C 2: N,N-dimethyl-formamide / dichloromethane / 4 h / Reflux 3: tetrahydrofuran / 2 h View Scheme

1,2-bis(chloroacetoxy)ethane (6941-69-1) + 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → ethane-1,2-diyl bis({[4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetate)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 72h; Time;	100%
With potassium hydrogencarbonate In ethanol at 50 - 55℃; Inert atmosphere;	92%

4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) + bromoacetic acid methyl ester (96-32-2) → 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-yl)thio)acetic acid methyl ester (1533519-85-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 3h;	99.5%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 4h;	85%
With sodium carbonate In N,N-dimethyl-formamide at 27 - 35℃; Concentration; Time; Temperature; Large scale;
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h;	4 g
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h;	4 g

ethane-1,2-diyl bis(2-bromoacetate) (3785-34-0) + 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → ethane-1,2-diyl bis({[4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetate)

Conditions	Yield
With potassium hydrogencarbonate In ethanol at 50 - 55℃; Inert atmosphere;	94%

phenyl 2-bromoacetate (620-72-4) + 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → phenyl 2‐((4‐(4‐cyclopropylnaphthalen‐1‐yl)‐4H‐1,2,4‐triazol‐3‐yl)thio)acetate

Conditions	Yield
Stage #1: 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol With triethylamine In isopropyl alcohol at 20℃; for 0.333333h; Stage #2: phenyl 2-bromoacetate In isopropyl alcohol at 0 - 20℃; for 2h;	92%

4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) + bromoacetic acid (79-08-3) → 2-[[4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]thio]acetic acid

Conditions	Yield
Stage #1: 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol With sodium hydrogencarbonate In ethanol; water at 25 - 45℃; Stage #2: bromoacetic acid In ethanol; water at 25 - 55℃; for 1h; Stage #3: With acetic acid In ethanol; water at 25 - 50℃;	91.9%

phenyl chloroacetate (620-73-5) + 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → phenyl 2‐((4‐(4‐cyclopropylnaphthalen‐1‐yl)‐4H‐1,2,4‐triazol‐3‐yl)thio)acetate

Conditions	Yield
Stage #1: 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol With triethylamine In acetone at 20℃; for 0.333333h; Stage #2: phenyl chloroacetate In isopropyl alcohol; acetone at 0 - 20℃; for 2h;	90%

4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-yl)thio)acetic acid methyl ester (1533519-85-5)

Conditions	Yield
With potassium phosphate In water; acetone at 40℃; for 6h;	90%

(R)-1-phenylethyl 2-bromoacetate (1046769-20-3) + 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → (R)-1-phenylethyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 15℃; for 3h;	87%
With potassium carbonate In N,N-dimethyl-formamide at 15℃; for 2.5h;

4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) + chloroacetic acid 2-[2-(2-chloro-acetoxy)-ethoxy]-ethyl ester (106-78-5) → C38H36N6O5S2

Conditions	Yield
In ethanol at 50 - 55℃; Inert atmosphere;	86%

chloroacetic acid 4-(2-chloroacetoxy)phenyl ester (10470-77-6) + 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → C40H32N6O4S2

Conditions	Yield
In acetonitrile at 50 - 55℃; Inert atmosphere;	83%

Methyl 3-bromopropionate (3395-91-3) + 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → C19H19N3O2S

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 96h; Autoclave;	67%

4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → Reaxys ID: 26486083

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide 2: N-Bromosuccinimide / tetrahydrofuran View Scheme

4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → 2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium carbonate / N,N-dimethyl-formamide / 27 - 35 °C / Large scale 2: N-Bromosuccinimide / tetrahydrofuran / 27 - 32 °C / Large scale View Scheme
Multi-step reaction with 2 steps 1: potassium phosphate / water; acetone / 6 h / 40 °C 2: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / ethyl acetate / Reflux View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N-Bromosuccinimide / tetrahydrofuran / 3 h / 30 - 32 °C View Scheme

4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → 2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium carbonate / N,N-dimethyl-formamide / 27 - 35 °C / Large scale 2: N-Bromosuccinimide / tetrahydrofuran / 27 - 32 °C / Large scale 3: sodium hydroxide; water / toluene / 18 - 25 °C View Scheme
Multi-step reaction with 4 steps 1: sodium carbonate / N,N-dimethyl-formamide / 27 - 35 °C / Large scale 2: N-Bromosuccinimide / tetrahydrofuran / 27 - 32 °C / Large scale 3: sodium hydroxide / toluene; water / 18 - 25 °C / Large scale 4: hydrogen bromide / water; ethyl acetate / 30 - 35 °C / pH 2 - 4 / Large scale View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / acetone / 0.33 h / 20 °C 1.2: 2 h / 0 - 20 °C 2.1: 1,1'-Thiocarbonyldiimidazole / dichloromethane / 0.25 h / 20 °C 3.1: sodium hydrogencarbonate / acetone / 12 h / 65 °C View Scheme

4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid sodium salt (1151516-14-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium carbonate / N,N-dimethyl-formamide / 27 - 35 °C / Large scale 2: N-Bromosuccinimide / tetrahydrofuran / 27 - 32 °C / Large scale 3: sodium hydroxide / toluene; water / 18 - 25 °C / Large scale View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N-Bromosuccinimide / tetrahydrofuran / 3 h / 30 - 32 °C 3: sodium hydroxide; water / tetrahydrofuran / 2 h View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 25 °C 2: sodium hydroxide; N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 25 °C 3: sodium hydroxide / ethanol; water / 2 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 20 °C 2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N-Bromosuccinimide / tetrahydrofuran / 3 h / 30 - 32 °C 3: sodium hydroxide / tetrahydrofuran; water / 2 h View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 50 °C 2: N-Bromosuccinimide / tetrahydrofuran / 2 - 32 °C 3: sodium hydroxide / toluene; water / 10 - 15 °C View Scheme

4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) + Reaxys ID: 26486092 → Reaxys ID: 26486087

Conditions	Yield
In N,N-dimethyl-formamide

4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (1533519-84-4) → phenyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine / isopropyl alcohol / 0.33 h / 20 °C 1.2: 2 h / 0 - 20 °C 2.1: 1,1'-Thiocarbonyldiimidazole / dichloromethane / 0.25 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: triethylamine / acetone / 0.33 h / 20 °C 1.2: 2 h / 0 - 20 °C 2.1: 1,1'-Thiocarbonyldiimidazole / dichloromethane / 0.25 h / 20 °C View Scheme

Upstream product

• 571-57-3 4-bromo-1-naphthol 
• 23719-80-4 cyclopropylmagnesium bromide 
• 2298-07-9 4-Bromo-1-naphthylamine 
• 1533519-86-6 N-(4-cyclopropylnaphthalen-1-yl)-2-formylhydrazine-1-thiocarboxamide 
• 1533519-91-3 tert-butyl 4-cyclopropylnaphthalen-1-ylcarbamate 
• 1533519-92-4 1-amino-4-cyclopropylnaphthalene hydrochloride 
• 878671-95-5 1-cyclopropylnaphthalene-4-yl isothiocyanate 
• 1533519-87-7 1-amino-4-cyclopropylnaphthalene oxalate 
• 878671-93-3 1-cyclopropyl-4-nitronaphthalene 
• 25033-19-6 1-cyclopropyl-naphthalene 
• 90-11-9 1-Bromonaphthalene 
• 878671-94-4 1-amino-4-cyclopropylnaphthalene 

Downstream Products

• 878672-00-5 2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid 
• 1533519-85-5 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-yl)thio)acetic acid methyl ester 
• 1533519-93-5 2-(4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid 
• 1158970-76-3 5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazole-3-thiol 
• 878672-00-5 (R)-2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid 
• 878672-00-5 (S)-2-((5-bromo-4-(4-cyclopropyl-1-naphthalenyl)-4H-1,2,4-triazol-3-yl)thio)-acetic acid 

Relevant articles and documents

A process for the preparation of intermediates to si Lei (by machine translation)

The invention discloses a compound of formula (I) the method for the preparation of intermediates shows Si Lei. The method can directly introduce triazazole functional group, the reaction yield is up to 96.30%, sulfur generation and avoid the use of toxic reagent such as phosgene. Furthermore, the synthetic route of this invention does not need to ring closing reaction step, a total of six-step reaction of the final product can be obtained, it is simple and convenient to prepare, low cost, is suitable for industrial production. (by machine translation)

MANUFACTURE OF 2- (5- BROMO-4 (-CYCLOPROPYLNAPHTHALEN-1-YL) -4H-1,2,4-TRIAZOL-3-YLTHIO) ACETIC ACID

Described herein are certain processes for the synthesis of compounds of Formula (I):