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Lonafarnib
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Name

Lonafarnib

 EINECS N/A
CAS No. 193275-84-2 Density 1.537 g/cm3
PSA 79.53000 LogP 6.48600
Solubility N/A Melting Point 214.5-215.9° (monohydrate); mp 222-223°
Formula C27H31Br2ClN4O2 Boiling Point 710.432 °C at 760 mmHg
Molecular Weight 638.83 Flash Point 383.455 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 193275-84-2 (LONAFARNIB) Hazard Symbols N/A
Synonyms

4-[2-[4-[(11R)-3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl]-1-piperidinyl]-2-oxoethyl]-1-piperidinecarboxamide;Sarasar;Sch 66336;

 

Lonafarnib Synthetic route

VI, N-α-t-boc L-asparagin

917-61-3

sodium isocyanate

193275-84-2

lonafarnib

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran; water at 20 - 50℃; for 4h;95%
1118-02-1

trimethylsilyl isocyanate

193276-77-6

(+)-4-(8-chloro-3,10-dibromo-6,11-dihydro-5H-benzo-<5,6>cyclohepta<1,2-b>pyridin-11(R)-yl)-1-<(4-piperidinyl)acetyl>piperidine

193275-84-2

lonafarnib

Conditions
ConditionsYield
In dichloromethane at 25℃; for 48h;82%
57-13-6

urea

193276-77-6

(+)-4-(8-chloro-3,10-dibromo-6,11-dihydro-5H-benzo-<5,6>cyclohepta<1,2-b>pyridin-11(R)-yl)-1-<(4-piperidinyl)acetyl>piperidine

193275-84-2

lonafarnib

Conditions
ConditionsYield
With sodium hydroxide In 1-methyl-pyrrolidin-2-one; ethanol at 110℃; for 10h; pH=9;5.44 g
157688-46-5

2-(1-(tert-butoxycarbonyl)piperidin-4-yl)acetic acid

193275-84-2

lonafarnib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide; toluene / 18 h / 20 °C
2: hydrochloric acid / ethanol / 6 h / 20 °C
3: 5.44 g / NaOH / ethanol; 1-methyl-pyrrolidin-2-one / 10 h / 110 °C / pH 9
View Scheme
Multi-step reaction with 3 steps
1: HOBT, DEC / dimethylformamide / 24 h / 25 °C
2: TFA / CH2Cl2 / 24 h / 25 °C
3: 82 percent / CH2Cl2 / 48 h / 25 °C
View Scheme
193276-55-0

3,10-dibromo-8-chloro-5,6-dihydro-11H-benzo<5,6>cyclohepta<1,2-b>pyridin-11-one

193275-84-2

lonafarnib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 84 percent / zinc dust; acetic anhydride; trifluoroacetic acid / tetrahydrofuran / 24 h / -25 - 18 °C
2.1: lithium diisopropylamide*THF; quinine; water / toluene; cyclohexane / 21 h / 5 - 25 °C
2.2: 10.5 g / sulfuric acid / toluene / 4 h / 85 °C
3.1: 80 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide; toluene / 18 h / 20 °C
4.1: hydrochloric acid / ethanol / 6 h / 20 °C
5.1: 5.44 g / NaOH / ethanol; 1-methyl-pyrrolidin-2-one / 10 h / 110 °C / pH 9
View Scheme
193276-49-2

(R)-(+)-(8-chloro-3,10-dibromo-6,11-dihydro-5H-benzo-<5,6>cyclohepta<1,2-b>pyridin-11-yl)-1-piperidine

193275-84-2

lonafarnib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide; toluene / 18 h / 20 °C
2: hydrochloric acid / ethanol / 6 h / 20 °C
3: 5.44 g / NaOH / ethanol; 1-methyl-pyrrolidin-2-one / 10 h / 110 °C / pH 9
View Scheme
Multi-step reaction with 3 steps
1: HOBT, DEC / dimethylformamide / 24 h / 25 °C
2: TFA / CH2Cl2 / 24 h / 25 °C
3: 82 percent / CH2Cl2 / 48 h / 25 °C
View Scheme
193276-76-5

(+)-1,1-dimethylethyl<<<4-(8-chloro-3,10-dibromo-6,11-dihydro-5H-benzo-<5,6>cyclohepta<1,2-b>pyridin-11(R)-yl)-1-piperidinyl>-carbonyl>-methyl>-1-piperidinecarboxylate

193275-84-2

lonafarnib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrochloric acid / ethanol / 6 h / 20 °C
2: 5.44 g / NaOH / ethanol; 1-methyl-pyrrolidin-2-one / 10 h / 110 °C / pH 9
View Scheme
Multi-step reaction with 2 steps
1: TFA / CH2Cl2 / 24 h / 25 °C
2: 82 percent / CH2Cl2 / 48 h / 25 °C
View Scheme
272107-22-9

8-chloro-3,10-dibromo-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridine

193275-84-2

lonafarnib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: lithium diisopropylamide*THF; quinine; water / toluene; cyclohexane / 21 h / 5 - 25 °C
1.2: 10.5 g / sulfuric acid / toluene / 4 h / 85 °C
2.1: 80 percent / 1-hydroxybenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / dimethylformamide; toluene / 18 h / 20 °C
3.1: hydrochloric acid / ethanol / 6 h / 20 °C
4.1: 5.44 g / NaOH / ethanol; 1-methyl-pyrrolidin-2-one / 10 h / 110 °C / pH 9
View Scheme
165740-12-5

ethyl 4-(3-bromo-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

193275-84-2

lonafarnib

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 86 percent / H2SO4, NaNO3 / 2 h / -5 °C
2: 85 percent / iron filings, CaCl2, H2O / ethanol / 16 h / Heating
3: 70 percent / Br2, AcOH / 16 h / Ambient temperature
4: 1.) conc HCl, NaNO2, 2.) 50 percent H3PO2 / 1.) from -10 deg C to 0 deg C, 2 h, 2.) RT, overnight
5: 93 percent / conc. HCl / 16 h / Heating
6: DIBAL-H / toluene / 0.67 h / Heating
8: HOBT, DEC / dimethylformamide / 24 h / 25 °C
9: TFA / CH2Cl2 / 24 h / 25 °C
10: 82 percent / CH2Cl2 / 48 h / 25 °C
View Scheme
193276-48-1

(8-chloro-3,10-dibromo-6,11-dihydro-5H-benzo-<5,6>cyclohepta<1,2-b>pyridin-11-yl)-1-piperidine

193275-84-2

lonafarnib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
2: HOBT, DEC / dimethylformamide / 24 h / 25 °C
3: TFA / CH2Cl2 / 24 h / 25 °C
4: 82 percent / CH2Cl2 / 48 h / 25 °C
View Scheme

Lonafarnib Specification

The Lonafarnib, with the CAS registry number 193275-84-2, is also known as 4-[2-[4-[(11R)-3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl]-1-piperidinyl]-2-oxoethyl]-1-piperidinecarboxamide. It belongs to the product category of APIs. This chemical's molecular formula is C27H31Br2ClN4O2 and molecular weight is 638.82. What's more, its systematic name is called 4-(2-{4-[(11R)-3,10-Dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl]piperidin-1-yl}-2-oxoethyl)piperidine-1-carboxamide. It is a farnesyl-OH-transferase inhibitor that is being investigated in a human clinical trial as a potential treatment for progeria.

Physical properties about Lonafarnib are: (1)ACD/LogP: 5.03; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 5.03; (4)ACD/LogD (pH 7.4): 5.03; (5)ACD/BCF (pH 5.5): 3906.11; (6)ACD/BCF (pH 7.4): 3913.16; (7)ACD/KOC (pH 5.5): 12952.08; (8)ACD/KOC (pH 7.4): 12975.44; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 56.75 Å2; (13)Index of Refraction: 1.63; (14)Molar Refractivity: 148 cm3; (15)Molar Volume: 415.7 cm3; (16)Surface Tension: 58.1 dyne/cm; (17)Density: 1.536 g/cm3; (18)Flash Point: 383.5 °C; (19)Enthalpy of Vaporization: 103.89 kJ/mol; (20)Boiling Point: 710.4 °C at 760 mmHg; (21)Vapour Pressure: 4.96E-20 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(N)N5CCC(CC(=O)N4CCC([C@@H]3c1c(Br)cc(Cl)cc1CCc2cc(Br)cnc23)CC4)CC5
(2) InChI: InChI=1S/C27H31Br2ClN4O2/c28-20-12-19-2-1-18-13-21(30)14-22(29)24(18)25(26(19)32-15-20)17-5-9-33(10-6-17)23(35)11-16-3-7-34(8-4-16)27(31)36/h12-17,25H,1-11H2,(H2,31,36)/t25-/m1/s1
(3) InChIKey: DHMTURDWPRKSOA-RUZDIDTESA-N

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