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Nevirapine
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Name

Nevirapine

 EINECS 603-345-0
CAS No. 129618-40-2 Density 1.351 g/cm3
PSA 63.57000 LogP 2.47830
Solubility 0.1g/L(temperature not stated) Melting Point 247 °C
Formula C15H14N4O Boiling Point 415.4 °C at 760 mmHg
Molecular Weight 266.302 Flash Point 205 °C
Transport Information N/A Appearance white or off-white crystalline powder
Safety 26-36-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 129618-40-2 (Nevirapine) Hazard Symbols IrritantXi
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);

Article Data 17

Nevirapine Synthetic route

133627-47-1

N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide

129618-40-2

Nevirapine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

Nevirapine Chemical Properties

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

Nevirapine 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.

Nevirapine Uses

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

Nevirapine 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.

Nevirapine Safety Profile

Hazard Codes: IrritantXi
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.

Nevirapine 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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