CAS No.129618-40-2,Nevirapine Suppliers

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Basic Information

Molecular Structure:
CAS No.:	129618-40-2
Name:	Nevirapine
Article Data:	17

Formula:	C₁₅H₁₄N₄O
Molecular Weight:	266.302
Synonyms:	11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido(3,2-b:2,3-e)(1,4)diazepin-6-one;Viramune;BIRG 0587;BI-RG-587;BI-RG-587;6H-Dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one,11-cyclopropyl-5,11-dihydro-4-methyl-;99% Nevirapine;Nevirapine [USAN:INN];BI-RG 587;BIRG 587;BIRG 0587;Viramune (TN);NVP;Nevirapine (JP14/USAN);11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido;Viramune (Nevirapine);
EINECS:	603-345-0
Density:	1.351 g/cm³
Melting Point:	247 °C
Boiling Point:	415.4 °C at 760 mmHg
Flash Point:	205 °C
Solubility:	0.1g/L(temperature not stated)
Appearance:	white or off-white crystalline powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36-37/39
PSA:	63.57000
LogP:	2.47830

Synthetic route

: 133627-47-1
N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
With diethylene glycol dimethyl ether; sodium hydride at 100 - 125℃; for 2.5h; Inert atmosphere;	96%
Stage #1: N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide With potassium tert-butylate In diethylene glycol dimethyl ether at 100 - 110℃; for 1.5h; Stage #2: With acetic acid In diethylene glycol dimethyl ether at 5 - 10℃; pH=6.0 - 7.0; Product distribution / selectivity;	83.39%
Stage #1: N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide With potassium tert-butylate In toluene at 100 - 110℃; for 3 - 3.5h; Stage #2: With sulfuric acid In water; toluene at 5 - 10℃; pH=1 - 7.0; Product distribution / selectivity;	79.96%

: methyl 2-(cyclopropylamino)nicotinate

: 133627-45-9
3-Amino-2-chloro-4-methylpyridine

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
With sodium hydride In diethylene glycol dimethyl ether at 65 - 165℃; Flow reactor; Green chemistry;	96%
Multi-step reaction with 2 steps 1.1: sodium hydride / 3.5 h / 30 - 60 °C / Inert atmosphere 1.2: 2 h / 55 - 65 °C / Inert atmosphere 2.1: sodium hydride; diethylene glycol dimethyl ether / 2.5 h / 100 - 125 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / diethylene glycol dimethyl ether / 0.5 h / 20 °C 1.2: 2 h / 60 °C 2.1: sodium hydride / diethylene glycol dimethyl ether / 4 h / 105 - 117 °C / Green chemistry View Scheme

: 162709-30-0
2-(Cyclopropylamino)-N-(2-methoxy-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
With pyridine; sodium hexamethyldisilazane at 90℃; for 6h;	91%

: 133627-46-0
2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

: 765-30-0
Cyclopropylamine

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Stage #1: 2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide; Cyclopropylamine With triethylamine In toluene at 130℃; for 10h; Autoclave; Stage #2: With sodium amide In diethylene glycol dimethyl ether at 15 - 110℃; for 2h; Temperature; Time; Reagent/catalyst; Autoclave;	86%
Stage #1: 2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide; Cyclopropylamine With calcium oxide In diethylene glycol dimethyl ether at 135 - 145℃; Stage #2: With sodium hydride at 140℃; for 0.5 - 1h; Stage #3: With water; acetic acid; ethyl acetate at 0 - 10℃; for 1 - 2h;

: 135575-99-4
2-chloro-11-cyclopropyl-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepine-6-one

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In diethylene glycol dimethyl ether at 100℃; under 2585.7 Torr; for 12h; Yield given;

: 49609-84-9
2-Chloronicotinoyl chloride

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, 23 h 2: 94 percent / 4 h / 140 °C 3: 67 percent / 80percent NaH / bis-(2-methoxy-ethyl) ether / 1.5 h / 185 °C View Scheme
Multi-step reaction with 3 steps 1: 65.5 percent / pyridine / cyclohexane; dioxane / 48 h / Ambient temperature 2: 83 percent / xylene / 18 h / 110 °C 3: 67 percent / NaH / various solvent(s) / 1.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: pyridine / acetonitrile / 20 - 45 °C 2: calcium oxide / xylene / 140 °C 3: sodium hydrogen sulfate; copper(l) iodide; sulfuric acid; potassium tert-butylate / diethylene glycol dimethyl ether / 115 °C View Scheme

: 2942-59-8
2-chloronicotinic acid

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 99 percent / thionyl chloride / 1 h / Heating 2: 87 percent / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, 23 h 3: 94 percent / 4 h / 140 °C 4: 67 percent / 80percent NaH / bis-(2-methoxy-ethyl) ether / 1.5 h / 185 °C View Scheme
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 60 - 65 °C 2: 5 h / 60 - 65 °C 3: 5%-palladium/activated carbon; hydrogen / ethanol; toluene / 6 h / 30 - 35 °C / 1500.15 - 2250.23 Torr / Autoclave 4: benzenesulfonic acid / 6 h / 90 - 95 °C View Scheme

: 23056-39-5
2-chloro-3-nitro-4-methylpyridine

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 98 percent / SnCl2 * 2 H2O, conc. HCl / diethyl ether / 0.33 h / Ambient temperature 2: 87 percent / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, 23 h 3: 94 percent / 4 h / 140 °C 4: 67 percent / 80percent NaH / bis-(2-methoxy-ethyl) ether / 1.5 h / 185 °C View Scheme
Multi-step reaction with 4 steps 1: 75 percent / H2 / 5percent Rh/C / ethanol / 3 h / 2585.7 Torr 2: 65.5 percent / pyridine / cyclohexane; dioxane / 48 h / Ambient temperature 3: 83 percent / xylene / 18 h / 110 °C 4: 67 percent / NaH / various solvent(s) / 1.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 5 h / 60 - 65 °C 2: 5%-palladium/activated carbon; hydrogen / ethanol; toluene / 6 h / 30 - 35 °C / 1500.15 - 2250.23 Torr / Autoclave 3: benzenesulfonic acid / 6 h / 90 - 95 °C View Scheme

: 133627-45-9
3-Amino-2-chloro-4-methylpyridine

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / CH2Cl2 / 1.) -78 deg C, 1 h, 2.) RT, 23 h 2: 94 percent / 4 h / 140 °C 3: 67 percent / 80percent NaH / bis-(2-methoxy-ethyl) ether / 1.5 h / 185 °C View Scheme
Multi-step reaction with 3 steps 1: 65.5 percent / pyridine / cyclohexane; dioxane / 48 h / Ambient temperature 2: 83 percent / xylene / 18 h / 110 °C 3: 67 percent / NaH / various solvent(s) / 1.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: pyridine / acetonitrile / 20 - 45 °C 2: calcium oxide / xylene / 140 °C 3: sodium hydrogen sulfate; copper(l) iodide; sulfuric acid; potassium tert-butylate / diethylene glycol dimethyl ether / 115 °C View Scheme

: 133627-46-0
2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / 4 h / 140 °C 2: 67 percent / 80percent NaH / bis-(2-methoxy-ethyl) ether / 1.5 h / 185 °C View Scheme
Multi-step reaction with 2 steps 1: 83 percent / xylene / 18 h / 110 °C 2: 67 percent / NaH / various solvent(s) / 1.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: calcium oxide / xylene / 140 °C 2: sodium hydrogen sulfate; copper(l) iodide; sulfuric acid; potassium tert-butylate / diethylene glycol dimethyl ether / 115 °C View Scheme

Raw Materials

765-30-0

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Chemistry

Molecular structure of Nevirapine (CAS NO.129618-40-2) is:

Product Name: Nevirapine
CAS Registry Number: 129618-40-2
Molecular Weight: 266.29786 [g/mol]
Molecular Formula: C₁₅H₁₄N₄O
XLogP3-AA: 2
H-Bond Donor: 1
H-Bond Acceptor: 4
Melting Point: 247 °C
Surface Tension: 66.3 dyne/cm
Density: 1.351 g/cm³
Flash Point: 205 °C
Enthalpy of Vaporization: 66.85 kJ/mol
Boiling Point: 415.4 °C at 760 mmHg
Vapour Pressure: 4.13E-07 mmHg at 25°C
Product Categories: Active Pharmaceutical Ingredients;API;Anti-virals;Inhibitors;Intermediates & Fine Chemicals;Non-nucleoside Reverse Transcriptase;Pharmaceuticals

History

Nevirapine (CAS NO.129618-40-2) was discovered by Hargrave et al. at Boehringer Ingelheim Pharmaceuticals, Inc., one of the Boehringer Ingelheim group of companies. It is covered by U.S. Patent 5,366,972 and corresponding foreign patents. It was the first NNRTI approved by the U.S. Food and Drug Administration (FDA). It was approved June 21, 1996 for adults and September 11, 1998 for children. It was also approved in Europe in 1997.

Uses

Nevirapine (CAS NO.129618-40-2) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) used to treat HIV-1 infection and AIDS.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD	oral	> 3200mg/kg (3200mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 41, Pg. 2209, 1999.
rat	LDLo	oral	400mg/kg (400mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 41, Pg. 2209, 1999.

Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.

Specification

Nevirapine , its cas register number is 129618-40-2. It also can be called Viramune ; 11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one ; 6H-Dipyrido(3,2-b:2',3'-e)(1,4)diazepin-6-one, 11-cyclopropyl-5,11-dihydro-4-methyl- .It is a crystalline solid. It has also been tested in trials in Africa, some of which have been highly controversial.

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