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Nevirapine Basic information Product Name: Nevirapine Synonyms: 11-CYCLOPROPYL-5,11-DIHYDRO-4-METHYL-6H-DIPYRIDO[3,2-B:2',3'-E][1,4]DIAZ
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inquiry1.Prompt Goods; 2.Flexible payment terms; 3.Documents & Certificate support. Name: Nevirapine Structure: Formula: C15H14N4O Molecular Weight : 266.3 Synonyms: 6H-DIPYRIDO[3,2-B:2',3'-E][1,4]DIAZEPIN-6-ONE,11-CYCLOPROPYL-5,11-DIHYD
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N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide
Nevirapine
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% |
3-Amino-2-chloro-4-methylpyridine
Nevirapine
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 |
2-(Cyclopropylamino)-N-(2-methoxy-4-methyl-3-pyridinyl)-3-pyridinecarboxamide
Nevirapine
Conditions | Yield |
---|---|
With pyridine; sodium hexamethyldisilazane at 90℃; for 6h; | 91% |
2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide
Cyclopropylamine
Nevirapine
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; |
2-chloro-11-cyclopropyl-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepine-6-one
Nevirapine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In diethylene glycol dimethyl ether at 100℃; under 2585.7 Torr; for 12h; Yield given; |
2-Chloronicotinoyl chloride
Nevirapine
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 |
2-chloronicotinic acid
Nevirapine
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 |
2-chloro-3-nitro-4-methylpyridine
Nevirapine
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 |
3-Amino-2-chloro-4-methylpyridine
Nevirapine
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 |
2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide
Nevirapine
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 |
tert-butyl methyl ether
2-chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide
Cyclopropylamine
Nevirapine
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 |
Nevirapine
Conditions | Yield |
---|---|
With strong base |
2-chloro-4-methyl-3-pyridinecarbonitrile
Nevirapine
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 |
2-chloro-4-methyl-3-pyridinecarboxamide
Nevirapine
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 |
2-chloro-3-pyridinecarbonitrile
Nevirapine
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 |
2-(cyclopropylamino)pyridine-3-carboxylic acid
Nevirapine
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 |
2-cyclopropylaminonicotinonitrile
Nevirapine
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 |
2-(4-(dimethylamino)but-3-en-2-ylidene)malononitrile
Nevirapine
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 |
isopropylidenemalonodinitrile
Nevirapine
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 |
3-amino-4-methylpyridine
Nevirapine
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 |
Nevirapine
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 |
Nevirapine
Conditions | Yield |
---|---|
With benzenesulfonic acid at 90 - 95℃; for 6h; Reagent/catalyst; | 12.6 g |
Nevirapine
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 |
4-Methyl-3-nitro-2-pyridone
Nevirapine
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 |
silver(I) acetate
Nevirapine
11-cyclopropyl-4-methyl-6-oxo-6,11-dihydro-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-2-yl acetate
Conditions | Yield |
---|---|
With iodine In dichloromethane at 104℃; for 0.0833333h; | 100% |
Conditions | Yield |
---|---|
In ethanol Mannich reaction; Irradiation; microwave; | 92% |
Conditions | Yield |
---|---|
In ethanol Mannich reaction; Irradiation; microwave; | 91% |
Conditions | Yield |
---|---|
In ethanol Mannich reaction; Irradiation; microwave; | 89% |
Conditions | Yield |
---|---|
In ethanol Mannich reaction; Irradiation; microwave; | 86% |
Conditions | Yield |
---|---|
In ethanol Mannich reaction; Irradiation; microwave; | 83% |
Conditions | Yield |
---|---|
In ethanol Mannich reaction; Irradiation; microwave; | 80% |
Nevirapine
Conditions | Yield |
---|---|
With N,N-dimethyl-aniline; trichlorophosphate at 110℃; for 8h; | 80% |
In toluene |
Conditions | Yield |
---|---|
In ethanol Mannich reaction; Irradiation; microwave; | 78% |
triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
Nevirapine
Conditions | Yield |
---|---|
With 1,2-dimethoxyethane; potassium hexamethylsilazane for 3h; Inert atmosphere; regioselective reaction; | 74% |
Conditions | Yield |
---|---|
In ethanol Mannich reaction; Irradiation; microwave; | 69% |
Conditions | Yield |
---|---|
In ethanol Mannich reaction; Irradiation; microwave; | 68% |
Nevirapine
d8-11-cyclopropyl-4-methyl-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6(11H)-one
Conditions | Yield |
---|---|
With water-d2; sodium formate; palladium 10% on activated carbon In 1,4-dioxane at 200℃; for 48h; | 58% |
Nevirapine
11-cyclopropyl-5,11-dihydro-4-(hydroxymethyl)-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepine-6-one
Conditions | Yield |
---|---|
With oxygen; lithium diisopropyl amide In tetrahydrofuran Ambient temperature; | 31% |
With MoO5*pyridine*HMPA; lithium diisopropyl amide Product distribution; multistep reaction; influence of base; | |
With MoO5*pyridine*HMPA; 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 MoO5*pyridine*HMPA; lithium diisopropyl amide 1.) THF, hexane, -30 deg C, 5 min, 2.) THF, hexane, -30 deg C, 1.5 h; Yield given. Multistep reaction; |
Nevirapine
11-cyclopropyl-5,11-dihydro-4-methyl-3-nitro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
Conditions | Yield |
---|---|
With nitronium tetrafluoborate; 4 A molecular sieve In acetonitrile at 0℃; for 20h; Nitration; | 20% |
Nevirapine
Conditions | Yield |
---|---|
With dihydrogen peroxide; acetic acid at 95℃; for 18h; | A 0.9% B 17% C 9% |
Nevirapine
11-cyclopropyl-7-iodo-4-methyl-5H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6(11H)-one
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% |
Nevirapine
11-cyclopropyl-5,11-dihydro-5-hydroxy-4-methyl-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepin-6-one
Conditions | Yield |
---|---|
In tetrahydrofuran; mineral oil | 9.5% |
Nevirapine
A
C22H25F2N7O
B
C22H25F2N7O
C
C22H25F2N7O
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% |
Nevirapine
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% |
Nevirapine
11-cyclopropyl-5,11-dihydro-5-hydroxy-4-methyl-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepin-6-one
Conditions | Yield |
---|---|
With MoO5*pyridine*HMPA; sodium hydride 1.) THF, r.t., 1 h, 2.) 0 deg C to r.t., 2 d; Yield given. Multistep reaction; |
Nevirapine
phenyldimethylsilyl chloride
A
11-cyclopropyl-5,11-dihydro-4-<(dimethylphenylsilyl)methyl>-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepine-6-one
B
11-cyclopropyl-5,11-dihydro-7-(dimethylphenylsilyl)-4-methyl-6H-dipyrido<3,2-b:2',3'-e><1,4>diazepine-6-one
Conditions | Yield |
---|---|
Product distribution; multistep reaction; reaction of nevirapine with phenyldimethylchlorosilane; | |
Yield given. Multistep reaction. Yields of byproduct given; |
Nevirapine
methyl iodide
5-Cyclopropyl-9,10-dimethyl-5,10-dihydro-4,5,6,10-tetraaza-dibenzo[a,d]cyclohepten-11-one
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; |
Nevirapine
2-amino-5,11-dihydro-4-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one
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 |
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