Nevirapine supplier | CasNO.129618-40-2

Name
Nevirapine
EINECS 603-345-0
CAS No. 129618-40-2
Article Data17
CAS DataBase
Density 1.351 g/cm³
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
Appearance white or off-white crystalline powder
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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);
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

: 1634-04-4
tert-butyl methyl ether

: 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
In ethanol; diethylene glycol dimethyl ether; cyclohexane; water; acetic acid
In diglyme (diethylene glycol-dimethylether); ethanol; diethylene glycol dimethyl ether; cyclohexane; water; acetic acid

...Expand

Reaxys ID: 19829874: Reaxys ID: 19829874

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
With strong base

: 65169-38-2
2-chloro-4-methyl-3-pyridinecarbonitrile

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sulfuric acid / 1.25 h / 40 - 105 °C 1.2: 70 - 75 °C 2.1: sodium hydroxide; bromine / toluene; water / 0 - 60 °C 3.1: sodium hydride / 3.5 h / 30 - 60 °C / Inert atmosphere 3.2: 2 h / 55 - 65 °C / Inert atmosphere 4.1: sodium hydride; diethylene glycol dimethyl ether / 2.5 h / 100 - 125 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / water / 8.25 h / 40 - 105 °C 2: sodium hydroxide; bromine / water / 2 h / 0 - 20 °C 3: sodium hydride / diethylene glycol dimethyl ether / 65 - 165 °C / Flow reactor; Green chemistry View Scheme
Multi-step reaction with 4 steps 1.1: sulfuric acid / water / 8.25 h / 40 - 105 °C 2.1: sodium hydroxide; bromine / water / 2 h / 0 - 20 °C 3.1: sodium hydride / diethylene glycol dimethyl ether / 0.5 h / 20 °C 3.2: 2 h / 60 °C 4.1: sodium hydride / diethylene glycol dimethyl ether / 4 h / 105 - 117 °C / Green chemistry View Scheme

: 152362-01-1
2-chloro-4-methyl-3-pyridinecarboxamide

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; bromine / toluene; water / 0 - 60 °C 2.1: sodium hydride / 3.5 h / 30 - 60 °C / Inert atmosphere 2.2: 2 h / 55 - 65 °C / Inert atmosphere 3.1: sodium hydride; diethylene glycol dimethyl ether / 2.5 h / 100 - 125 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; bromine / water / 2 h / 0 - 20 °C 2.1: sodium hydride / diethylene glycol dimethyl ether / 0.5 h / 20 °C 2.2: 2 h / 60 °C 3.1: sodium hydride / diethylene glycol dimethyl ether / 4 h / 105 - 117 °C / Green chemistry View Scheme

: 6602-54-6
2-chloro-3-pyridinecarbonitrile

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: triethylamine / water; isopropyl alcohol / 140 °C / 517.16 - 3102.97 Torr / Inert atmosphere 2.1: water; potassium hydroxide / isopropyl alcohol / 12 h / 80 °C 3.1: thionyl chloride / toluene / 0.58 h / 20 - 50 °C / Inert atmosphere 3.2: 40 - 50 °C 4.1: sodium hydride / 3.5 h / 30 - 60 °C / Inert atmosphere 4.2: 2 h / 55 - 65 °C / Inert atmosphere 5.1: sodium hydride; diethylene glycol dimethyl ether / 2.5 h / 100 - 125 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: triethylamine / water; isopropyl alcohol / 6 h / 140 °C / 517.16 - 3102.97 Torr / Inert atmosphere 2.1: potassium hydroxide / 12 h / 20 - 40 °C 3.1: thionyl chloride / toluene / 0.5 h / 20 - 50 °C / Inert atmosphere 3.2: 2 h / 50 °C / Inert atmosphere 4.1: sodium hydride / diethylene glycol dimethyl ether / 65 - 165 °C / Flow reactor; Green chemistry View Scheme
Multi-step reaction with 5 steps 1.1: triethylamine / water; isopropyl alcohol / 6 h / 140 °C / 517.16 - 3102.97 Torr / Inert atmosphere 2.1: potassium hydroxide / 12 h / 20 - 40 °C 3.1: thionyl chloride / toluene / 0.5 h / 20 - 50 °C / Inert atmosphere 3.2: 2 h / 50 °C / Inert atmosphere 4.1: sodium hydride / diethylene glycol dimethyl ether / 0.5 h / 20 °C 4.2: 2 h / 60 °C 5.1: sodium hydride / diethylene glycol dimethyl ether / 4 h / 105 - 117 °C / Green chemistry View Scheme

: 639807-18-4
2-(cyclopropylamino)pyridine-3-carboxylic acid

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / toluene / 0.58 h / 20 - 50 °C / Inert atmosphere 1.2: 40 - 50 °C 2.1: sodium hydride / 3.5 h / 30 - 60 °C / Inert atmosphere 2.2: 2 h / 55 - 65 °C / Inert atmosphere 3.1: sodium hydride; diethylene glycol dimethyl ether / 2.5 h / 100 - 125 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: thionyl chloride / toluene / 0.5 h / 20 - 50 °C / Inert atmosphere 1.2: 2 h / 50 °C / Inert atmosphere 2.1: sodium hydride / diethylene glycol dimethyl ether / 65 - 165 °C / Flow reactor; Green chemistry View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride / toluene / 0.5 h / 20 - 50 °C / Inert atmosphere 1.2: 2 h / 50 °C / Inert atmosphere 2.1: sodium hydride / diethylene glycol dimethyl ether / 0.5 h / 20 °C 2.2: 2 h / 60 °C 3.1: sodium hydride / diethylene glycol dimethyl ether / 4 h / 105 - 117 °C / Green chemistry 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

: 52583-90-1
2-cyclopropylaminonicotinonitrile

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: water; potassium hydroxide / isopropyl alcohol / 12 h / 80 °C 2.1: thionyl chloride / toluene / 0.58 h / 20 - 50 °C / Inert atmosphere 2.2: 40 - 50 °C 3.1: sodium hydride / 3.5 h / 30 - 60 °C / Inert atmosphere 3.2: 2 h / 55 - 65 °C / Inert atmosphere 4.1: sodium hydride; diethylene glycol dimethyl ether / 2.5 h / 100 - 125 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: potassium hydroxide / 12 h / 20 - 40 °C 2.1: thionyl chloride / toluene / 0.5 h / 20 - 50 °C / Inert atmosphere 2.2: 2 h / 50 °C / Inert atmosphere 3.1: sodium hydride / diethylene glycol dimethyl ether / 65 - 165 °C / Flow reactor; Green chemistry View Scheme
Multi-step reaction with 4 steps 1.1: potassium hydroxide / 12 h / 20 - 40 °C 2.1: thionyl chloride / toluene / 0.5 h / 20 - 50 °C / Inert atmosphere 2.2: 2 h / 50 °C / Inert atmosphere 3.1: sodium hydride / diethylene glycol dimethyl ether / 0.5 h / 20 °C 3.2: 2 h / 60 °C 4.1: sodium hydride / diethylene glycol dimethyl ether / 4 h / 105 - 117 °C / Green chemistry View Scheme

: 71493-72-6
2-(4-(dimethylamino)but-3-en-2-ylidene)malononitrile

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogenchloride / 2 h / 50 - 55 °C 2.1: sulfuric acid / 1.25 h / 40 - 105 °C 2.2: 70 - 75 °C 3.1: sodium hydroxide; bromine / toluene; water / 0 - 60 °C 4.1: sodium hydride / 3.5 h / 30 - 60 °C / Inert atmosphere 4.2: 2 h / 55 - 65 °C / Inert atmosphere 5.1: sodium hydride; diethylene glycol dimethyl ether / 2.5 h / 100 - 125 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: hydrogenchloride / toluene / 20 - 55 °C 2: sulfuric acid / water / 8.25 h / 40 - 105 °C 3: sodium hydroxide; bromine / water / 2 h / 0 - 20 °C 4: sodium hydride / diethylene glycol dimethyl ether / 65 - 165 °C / Flow reactor; Green chemistry View Scheme
Multi-step reaction with 5 steps 1.1: hydrogenchloride / toluene / 20 - 55 °C 2.1: sulfuric acid / water / 8.25 h / 40 - 105 °C 3.1: sodium hydroxide; bromine / water / 2 h / 0 - 20 °C 4.1: sodium hydride / diethylene glycol dimethyl ether / 0.5 h / 20 °C 4.2: 2 h / 60 °C 5.1: sodium hydride / diethylene glycol dimethyl ether / 4 h / 105 - 117 °C / Green chemistry View Scheme

: 13166-10-4
isopropylidenemalonodinitrile

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: triethylamine; acetic anhydride / toluene / 2 h / 5 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / 2 h / 50 - 55 °C 3.1: sulfuric acid / 1.25 h / 40 - 105 °C 3.2: 70 - 75 °C 4.1: sodium hydroxide; bromine / toluene; water / 0 - 60 °C 5.1: sodium hydride / 3.5 h / 30 - 60 °C / Inert atmosphere 5.2: 2 h / 55 - 65 °C / Inert atmosphere 6.1: sodium hydride; diethylene glycol dimethyl ether / 2.5 h / 100 - 125 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: acetic anhydride / toluene / 5 - 10 °C / Inert atmosphere 1.2: 2 h / 5 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / toluene / 20 - 55 °C 3.1: sulfuric acid / water / 8.25 h / 40 - 105 °C 4.1: sodium hydroxide; bromine / water / 2 h / 0 - 20 °C 5.1: sodium hydride / diethylene glycol dimethyl ether / 65 - 165 °C / Flow reactor; Green chemistry View Scheme
Multi-step reaction with 6 steps 1.1: acetic anhydride / toluene / 5 - 10 °C / Inert atmosphere 1.2: 2 h / 5 - 20 °C / Inert atmosphere 2.1: hydrogenchloride / toluene / 20 - 55 °C 3.1: sulfuric acid / water / 8.25 h / 40 - 105 °C 4.1: sodium hydroxide; bromine / water / 2 h / 0 - 20 °C 5.1: sodium hydride / diethylene glycol dimethyl ether / 0.5 h / 20 °C 5.2: 2 h / 60 °C 6.1: sodium hydride / diethylene glycol dimethyl ether / 4 h / 105 - 117 °C / Green chemistry View Scheme

: 3430-27-1
3-amino-4-methylpyridine

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride; dihydrogen peroxide / water / 20 °C 1.2: pH 8 2.1: pyridine / acetonitrile / 20 - 45 °C 3.1: calcium oxide / xylene / 140 °C 4.1: sodium hydrogen sulfate; copper(l) iodide; sulfuric acid; potassium tert-butylate / diethylene glycol dimethyl ether / 115 °C View Scheme

: C8H12BrNO5

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: ammonium hydroxide / 5 h / 40 - 45 °C 2: trichlorophosphate / 1,2-dichloro-ethane / 8 h / 70 - 75 °C 3: 5 h / 60 - 65 °C 4: 5%-palladium/activated carbon; hydrogen / ethanol; toluene / 6 h / 30 - 35 °C / 1500.15 - 2250.23 Torr / Autoclave 5: benzenesulfonic acid / 6 h / 90 - 95 °C View Scheme

: C15H16N4O2

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
With benzenesulfonic acid at 90 - 95℃; for 6h; Reagent/catalyst;	12.6 g

: C8H12ClNO5

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: ammonium hydroxide / 5 h / 50 - 55 °C 2: trichlorophosphate / 1,2-dichloro-ethane / 8 h / 70 - 75 °C 3: 5 h / 60 - 65 °C 4: 5%-palladium/activated carbon; hydrogen / ethanol; toluene / 6 h / 30 - 35 °C / 1500.15 - 2250.23 Torr / Autoclave 5: benzenesulfonic acid / 6 h / 90 - 95 °C View Scheme

: 21901-18-8
4-Methyl-3-nitro-2-pyridone

: 129618-40-2
Nevirapine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: trichlorophosphate / 1,2-dichloro-ethane / 8 h / 70 - 75 °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

: 563-63-3
silver(I) acetate

: 129618-40-2
Nevirapine

: 1350539-29-5
11-cyclopropyl-4-methyl-6-oxo-6,11-dihydro-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-2-yl acetate

Conditions

Conditions	Yield
With iodine In dichloromethane at 104℃; for 0.0833333h;	100%

: 50-00-0
formaldehyd

: 6269-89-2
1-(4-Nitrophenyl)piperazine

: 129618-40-2
Nevirapine

: 5-cyclopropyl-9-methyl-10-[4-(4-nitro-phenyl)-piperazin-1-ylmethyl]-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one

Conditions

Conditions	Yield
In ethanol Mannich reaction; Irradiation; microwave;	92%

...Expand

: 50-00-0
formaldehyd

: 92-54-6
4-phenyl-1-piperazine

: 129618-40-2
Nevirapine

: 11-cyclopropyl-4-methyl-5-[(4-phenylpiperazin-1-yl)methyl]-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one

Conditions

Conditions	Yield
In ethanol Mannich reaction; Irradiation; microwave;	91%

...Expand

: 50-00-0
formaldehyd

: 38212-33-8
4-(4-chlorophenyl) piperazine

: 129618-40-2
Nevirapine

: 5-{[4-(4-chlorophenyl)piperazin-1-yl]methyl}-11-cyclopropyl-4-methyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one

Conditions

Conditions	Yield
In ethanol Mannich reaction; Irradiation; microwave;	89%

...Expand

: 50-00-0
formaldehyd

: 38212-30-5
1-(4-methoxyphenyl)piperazine

: 129618-40-2
Nevirapine

: 11-cyclopropyl-5-{[4-(4-methoxyphenyl)piperazin-1-yl]methyl}-4-methyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one

Conditions

Conditions	Yield
In ethanol Mannich reaction; Irradiation; microwave;	86%

...Expand

: 50-00-0
formaldehyd

: 2759-28-6
1-phenylmethylpiperazine

: 129618-40-2
Nevirapine

: 5-[(4-benzylpiperazin-1-yl)methyl]-11-cyclopropyl-4-methyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one

Conditions

Conditions	Yield
In ethanol Mannich reaction; Irradiation; microwave;	83%

...Expand

: 109-01-3
1-methyl-piperazine

: 50-00-0
formaldehyd

: 129618-40-2
Nevirapine

: 11-cyclopropyl-4-methyl-5-[4-methylpiperazin-1-yl]methyl-5,11-dihydro-6H-dipyrido[2,3-e:3',2'-b][1,4]diazepin-6-one

Conditions

Conditions	Yield
In ethanol Mannich reaction; Irradiation; microwave;	80%

...Expand

: 129618-40-2
Nevirapine

: 6-chloro-11-cyclopropyl-4-methyl-11H-dipyrido[3,2-b:2',3'-e][1,4]diazepine

Conditions

Conditions	Yield
With N,N-dimethyl-aniline; trichlorophosphate at 110℃; for 8h;	80%
In toluene

: 50-00-0
formaldehyd

: 129618-40-2
Nevirapine

: 2252-63-3
1-(4-Fluorophenyl)piperazine

: 5-cyclopropyl-10-[4-(4-fluoro-phenyl)-piperazin-1-ylmethyl]-9-methyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one

Conditions

Conditions	Yield
In ethanol Mannich reaction; Irradiation; microwave;	78%

...Expand

: 745783-97-5
triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

: 129618-40-2
Nevirapine

: 11-cyclopropyl-4-methyl-9-(triethylsilyl)-5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Conditions

Conditions	Yield
With 1,2-dimethoxyethane; potassium hexamethylsilazane for 3h; Inert atmosphere; regioselective reaction;	74%

: 50-00-0
formaldehyd

: 129618-40-2
Nevirapine

: 6640-24-0
N-(m-chlorophenyl)piperazine

: 10-[4-(3-chloro-phenyl)-piperazin-1-ylmethyl]-5-cyclopropyl-9-methyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one

Conditions

Conditions	Yield
In ethanol Mannich reaction; Irradiation; microwave;	69%

...Expand

: 110-85-0
piperazine

: 50-00-0
formaldehyd

: 129618-40-2
Nevirapine

: 5-cyclopropyl-9-methyl-10-piperazin-1-ylmethyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one

Conditions

Conditions	Yield
In ethanol Mannich reaction; Irradiation; microwave;	68%

...Expand

: 129618-40-2
Nevirapine

: 1051418-86-0
d8-11-cyclopropyl-4-methyl-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6(11H)-one

Conditions

Conditions	Yield
With water-d2; sodium formate; palladium 10% on activated carbon In 1,4-dioxane at 200℃; for 48h;	58%

: 129618-40-2
Nevirapine

: 133627-24-4
11-cyclopropyl-5,11-dihydro-4-(hydroxymethyl)-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepine-6-one

Conditions

Conditions	Yield
With oxygen; lithium diisopropyl amide In tetrahydrofuran Ambient temperature;	31%
With MoO5pyridineHMPA; lithium diisopropyl amide Product distribution; multistep reaction; influence of base;
With MoO5pyridineHMPA; lithium diisopropyl amide 1.) THF, hexane, below -40 deg C, 5 min, 2.) -30 to -40 deg C, 75 min; Yield given. Multistep reaction;
With MoO5pyridineHMPA; lithium diisopropyl amide 1.) THF, hexane, -30 deg C, 5 min, 2.) THF, hexane, -30 deg C, 1.5 h; Yield given. Multistep reaction;

: 129618-40-2
Nevirapine

: 284686-16-4
11-cyclopropyl-5,11-dihydro-4-methyl-3-nitro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Conditions

Conditions	Yield
With nitronium tetrafluoborate; 4 A molecular sieve In acetonitrile at 0℃; for 20h; Nitration;	20%

: 129618-40-2
Nevirapine

A: 5-Cyclopropyl-9-methyl-4-oxy-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one

B: 5-Cyclopropyl-9-methyl-6-oxy-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one

C: 11-cyclopropyl-5,11-dihydro-4-methyl-8-hydroxy-1,10-dioxy-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepin-6-one

Conditions

Conditions	Yield
With dihydrogen peroxide; acetic acid at 95℃; for 18h;	A 0.9% B 17% C 9%

...Expand

: 129618-40-2
Nevirapine

: 1227201-82-2
11-cyclopropyl-7-iodo-4-methyl-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6(11H)-one

Conditions

Conditions	Yield
Stage #1: Nevirapine With dilithium magnesium bis(2,2,6,6-tetramethylpiperidin-1-ide) dichloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	10%

oxodiperoxymolybdenum(pyridine)hexamethylphosphoramide: oxodiperoxymolybdenum(pyridine)hexamethylphosphoramide

: 129618-40-2
Nevirapine

: 135794-73-9
11-cyclopropyl-5,11-dihydro-5-hydroxy-4-methyl-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepin-6-one

Conditions

Conditions	Yield
In tetrahydrofuran; mineral oil	9.5%

: sodium 7‐azido‐1,1‐difluoroheptane‐1‐sulfinate

: 129618-40-2
Nevirapine

A: 1450912-75-0
C22H25F2N7O

B: 1450912-76-1
C22H25F2N7O

C: 1450912-74-9
C22H25F2N7O

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; trifluoroacetic acid; zinc(II) chloride In water; dimethyl sulfoxide at 50℃; for 11h; Cooling with ice;	A 8% B 9% C 9%

...Expand

: 129618-40-2
Nevirapine

: 11-cyclopropyl-5,11-dihydro-8-hydroxy-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Conditions

Conditions	Yield
Stage #1: Nevirapine With dihydrogen peroxide; acetic acid at 95 - 100℃; for 48h; Oxidation; Stage #2: With hydrogen; palladium on activated charcoal In ethyl acetate under 2068.59 Torr; for 6h; Reduction;	5%

: 129618-40-2
Nevirapine

: 135794-73-9
11-cyclopropyl-5,11-dihydro-5-hydroxy-4-methyl-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepin-6-one

Conditions

Conditions	Yield
With MoO5pyridineHMPA; sodium hydride 1.) THF, r.t., 1 h, 2.) 0 deg C to r.t., 2 d; Yield given. Multistep reaction;

: 129618-40-2
Nevirapine

: 768-33-2
phenyldimethylsilyl chloride

A: 141319-44-0
11-cyclopropyl-5,11-dihydro-4-<(dimethylphenylsilyl)methyl>-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepine-6-one

B: 141319-45-1
11-cyclopropyl-5,11-dihydro-7-(dimethylphenylsilyl)-4-methyl-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepine-6-one

Conditions

Conditions	Yield
Product distribution; multistep reaction; reaction of nevirapine with phenyldimethylchlorosilane;
Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 129618-40-2
Nevirapine

: 74-88-4
methyl iodide

: 133627-19-7
5-Cyclopropyl-9,10-dimethyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one

Conditions

Conditions	Yield
With sodium hydride 1.) DMSO, 2.) DMSO; Multistep reaction;
Stage #1: Nevirapine With sodium hydride In N,N-dimethyl-formamide at 60℃; for 2h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 2h;

: 129618-40-2
Nevirapine

: 284686-15-3
2-amino-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 20 percent / 4A molecular sieves; nitronium tetrafluoroborate / acetonitrile / 20 h / 0 °C 2: 86 percent / tin(II) chloride; conc. aq. HCl; acetic acid / 20 °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: 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.

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.

Product Name

Nevirapine

Synthetic route

Nevirapine Chemical Properties

Nevirapine History

Nevirapine Uses

Nevirapine Toxicity Data With Reference

Nevirapine Safety Profile

Nevirapine Specification

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