CAS No.193275-84-2,LONAFARNIB Suppliers

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Basic Information

Molecular Structure:
CAS No.:	193275-84-2
Name:	LONAFARNIB

Formula:	C₂₇H₃₁Br₂ClN₄O₂
Molecular Weight:	638.83
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;
Density:	1.537 g/cm³
Melting Point:	214.5-215.9° (monohydrate); mp 222-223°
Boiling Point:	710.432 °C at 760 mmHg
Flash Point:	383.455 °C
PSA:	79.53000
LogP:	6.48600

Synthetic route

: VI, N-α-t-boc L-asparagin

: 917-61-3
sodium isocyanate

: 193275-84-2
lonafarnib

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Raw Materials

157688-46-5

57-13-6

1118-02-1

272107-22-9

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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