6-fluoro-3-hydroxy-2-cyanopyrazine
favipiravir
Conditions | Yield |
---|---|
Stage #1: 6-fluoro-3-hydroxy-2-cyanopyrazine With sulfuric acid at 50℃; for 4h; Stage #2: With water at 3 - 10℃; for 0.666667h; Stage #3: With sodium hydroxide In water at 10℃; for 0.75h; | 92.3% |
With sodium hydroxide In water at 5 - 45℃; for 5.5h; Large scale; | 91% |
With sulfuric acid at 50℃; for 4h; | 68.43% |
Stage #1: 6-fluoro-3-hydroxy-2-cyanopyrazine With dihydrogen peroxide; sodium hydroxide at 10 - 20℃; for 1h; Stage #2: With N-ethyl-N,N-diisopropylamine In ethyl acetate at 80℃; for 1h; Reagent/catalyst; |
favipiravir
Conditions | Yield |
---|---|
With ammonium carbonate Reagent/catalyst; | 92.3% |
3,6-difluoro-2-pyrazinecarboxamide
favipiravir
Conditions | Yield |
---|---|
With water; sodium hydroxide at 60℃; for 3h; | 92.1% |
With sodium hydrogencarbonate In 1,4-dioxane; water at 60℃; for 8h; | 82% |
With water; sodium hydrogencarbonate at 50℃; for 8.5h; | 65% |
3,6-difluoropyrazine-2-carbonitrile
favipiravir
Conditions | Yield |
---|---|
Stage #1: 3,6-difluoropyrazine-2-carbonitrile With sodium acetate In tetrahydrofuran; water for 20h; Reflux; Stage #2: With dihydrogen peroxide; sodium hydroxide In water; toluene at 0 - 20℃; for 4h; | 89.6% |
Multi-step reaction with 2 steps 1.1: sodium acetate; water / toluene; dimethyl sulfoxide / 7 h / 50 °C 2.1: sulfuric acid / 4 h / 50 °C 2.2: 0.67 h / 3 - 10 °C 2.3: 0.75 h / 10 °C View Scheme | |
Multi-step reaction with 2 steps 1: hydrogenchloride / tetrahydrofuran / 1.5 h / 60 °C 2: sodium hydrogencarbonate / 1,4-dioxane; water / 8 h / 60 °C View Scheme |
dicyclohexylamine salt
favipiravir
Conditions | Yield |
---|---|
Stage #1: dicyclohexylamine salt With water; sodium hydroxide In toluene at 20℃; for 0.5h; Stage #2: With dihydrogen peroxide In toluene at 15 - 25℃; for 0.5h; | 84% |
Stage #1: dicyclohexylamine salt With sodium hydroxide In water; toluene at 15 - 25℃; for 0.5h; Stage #2: With water; dihydrogen peroxide at 15 - 30℃; Stage #3: With hydrogenchloride In water |
favipiravir
Conditions | Yield |
---|---|
With ammonia; sodium In tetrahydrofuran at -70 - -65℃; | 72% |
2-hydroxypyrazine-3-carboxamide
favipiravir
Conditions | Yield |
---|---|
With 1-fluoro-4-methyl-1,4-diazoniabicyclo<2.2.2>octane ditetrafluoroborate In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 70 - 80℃; for 20h; Reagent/catalyst; Solvent; Temperature; | 71.3% |
With fluorine In water | |
Multi-step reaction with 5 steps 1.1: bromine / acetonitrile / 6 h / 0 - 40 °C 2.1: trichlorophosphate / chlorobenzene / 0.5 h / 60 °C 2.2: 2.67 h / 90 - 100 °C 3.1: potassium fluoride; tetrabutylammomium bromide / toluene; dimethyl sulfoxide / 2.5 h / 60 °C 4.1: sodium acetate; water / toluene; dimethyl sulfoxide / 7 h / 50 °C 5.1: sulfuric acid / 4 h / 50 °C 5.2: 0.67 h / 3 - 10 °C 5.3: 0.75 h / 10 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: pyridine; N-chloro-succinimide / acetonitrile / 4 h / 80 - 85 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine; phosphorus(V) oxybromide / chlorobenzene / 4 h / 0 °C / Reflux 3.1: potassium fluoride / N,N-dimethyl-formamide / 20 h / 80 - 85 °C 4.1: sodium acetate / tetrahydrofuran; water / 20 h / Reflux 4.2: 4 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetonitrile / 55 - 60 °C 2.1: formic acid / 5 - 10 °C 2.2: 5 - 8 °C 3.1: ammonia; sodium / tetrahydrofuran / -70 - -65 °C View Scheme |
favipiravir
Conditions | Yield |
---|---|
With potassium fluoride; 18-crown-6 ether In toluene at 100℃; for 20h; | 15.96% |
Multi-step reaction with 4 steps 1.1: trichlorophosphate / chlorobenzene / 0.5 h / 60 °C 1.2: 2.67 h / 90 - 100 °C 2.1: potassium fluoride; tetrabutylammomium bromide / toluene; dimethyl sulfoxide / 2.5 h / 60 °C 3.1: sodium acetate; water / toluene; dimethyl sulfoxide / 7 h / 50 °C 4.1: sulfuric acid / 4 h / 50 °C 4.2: 0.67 h / 3 - 10 °C 4.3: 0.75 h / 10 °C View Scheme | |
Multi-step reaction with 4 steps 1: trichlorophosphate; N-ethyl-N,N-diisopropylamine / water / 8 h / 60 - 100 °C 2: potassium fluoride; tetrabutylammomium bromide / toluene; dimethyl sulfoxide / 3 h / 55 °C 3: dihydrogen peroxide / toluene; dimethyl sulfoxide / 2 h / 27 °C / Cooling with ice 4: sodium hydrogencarbonate; water / 8.5 h / 50 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: trichlorophosphate / 0.25 h / 70 °C 1.2: 6 h / 20 - 100 °C 1.3: 1 h 2.1: potassium fluoride dihydrate; tetrabutylammomium bromide / dimethyl sulfoxide / 3 h / 50 °C 3.1: potassium carbonate; dihydrogen peroxide / dimethyl sulfoxide; water / 1.5 h / 25 °C 4.1: sodium hydrogencarbonate; water / dimethyl sulfoxide / 8 h / 50 °C View Scheme | |
Multi-step reaction with 3 steps 1: diethylamino-sulfur trifluoride / dichloromethane / 5 h / 0 °C 2: 18-crown-6 ether; potassium fluoride / toluene / 20 h / 110 °C 3: methanol; sodium hydrogencarbonate; water / 8 h / 50 °C View Scheme |
favipiravir
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; sodium chloride; sodium thiosulfate In chloroform; water; acetonitrile | |
With chloro-trimethyl-silane; sodium iodide; sodium chloride; sodium thiosulfate In chloroform; water; acetonitrile |
methyl 6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarboxylate
favipiravir
Conditions | Yield |
---|---|
With sodium bicarbonate; sodium chloride; ammonia In methanol; water; ethyl acetate |
6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarbonitrile
favipiravir
Conditions | Yield |
---|---|
With sodium hydroxide; sulfuric acid; dihydrogen peroxide In water |
3-amino-6-fluoro-2-pyrazinecarboxamide
favipiravir
Conditions | Yield |
---|---|
With sodium bicarbonate; sodium chloride; sulfuric acid; sodium nitrite In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; di-isopropyl ether; water; ethyl acetate |
3,6-dichloropyrazine-2-carbonitrile
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium fluoride; tetrabutylammomium bromide / toluene; dimethyl sulfoxide / 2.5 h / 60 °C 2.1: sodium acetate; water / toluene; dimethyl sulfoxide / 7 h / 50 °C 3.1: sulfuric acid / 4 h / 50 °C 3.2: 0.67 h / 3 - 10 °C 3.3: 0.75 h / 10 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium fluoride; tetrabutylammomium bromide / dimethyl sulfoxide / 3 h / 55 °C / Sealed tube 2: dihydrogen peroxide / 2 h / 27 °C 3: sodium hydrogencarbonate; water / 8.5 h / 50 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium fluoride; tetrabutylammomium bromide / toluene; dimethyl sulfoxide / 3 h / 55 °C 2: dihydrogen peroxide / toluene; dimethyl sulfoxide / 2 h / 27 °C / Cooling with ice 3: sodium hydrogencarbonate; water / 8.5 h / 50 °C View Scheme |
C9H8ClN3O3
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium fluoride / dimethyl sulfoxide / 4 h / 90 °C 2.1: sodium hydrogencarbonate; water / 4 h / 100 °C 2.2: 1.17 h / 20 °C 3.1: water; sodium hydroxide / toluene / 0.5 h / 20 °C 3.2: 0.5 h / 15 - 25 °C View Scheme |
C9H8FN3O3
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate; water / 4 h / 100 °C 1.2: 1.17 h / 20 °C 2.1: water; sodium hydroxide / toluene / 0.5 h / 20 °C 2.2: 0.5 h / 15 - 25 °C View Scheme |
C9H10N4O6S
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium fluoride / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere 1.2: 3 h / 80 °C 1.3: 20 °C 2.1: water; sodium hydroxide / toluene / 0.5 h / 20 °C 2.2: 0.5 h / 15 - 25 °C View Scheme |
C9H12N2O4
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: acetyl chloride; isopentyl nitrite / isopropyl alcohol / 1.5 h / 5 - 40 °C / Inert atmosphere 2.1: trichlorophosphate / toluene; N,N-dimethyl-formamide / 7 h / 15 - 70 °C / Inert atmosphere 3.1: potassium fluoride / dimethyl sulfoxide / 4 h / 90 °C 4.1: sodium hydrogencarbonate; water / 4 h / 100 °C 4.2: 1.17 h / 20 °C 5.1: water; sodium hydroxide / toluene / 0.5 h / 20 °C 5.2: 0.5 h / 15 - 25 °C View Scheme |
C9H11N3O5
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: trichlorophosphate / toluene; N,N-dimethyl-formamide / 7 h / 15 - 70 °C / Inert atmosphere 2.1: potassium fluoride / dimethyl sulfoxide / 4 h / 90 °C 3.1: sodium hydrogencarbonate; water / 4 h / 100 °C 3.2: 1.17 h / 20 °C 4.1: water; sodium hydroxide / toluene / 0.5 h / 20 °C 4.2: 0.5 h / 15 - 25 °C View Scheme |
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: trifluoroacetic acid; hydroxylamine hydrochloride / methanol / 5 h / 10 °C / Inert atmosphere; Reflux 2.1: toluene-4-sulfonic acid; acetic acid / 2 h / 77 - 80 °C / Industrial scale 3.1: trichlorophosphate; triethylamine hydrochloride / 4 h / 85 °C 4.1: triethylamine / 2 h / 80 °C 5.1: potassium fluoride / dimethyl sulfoxide / 4 h / 90 °C 6.1: sodium hydrogencarbonate; water / 4 h / 100 °C 6.2: 1.17 h / 20 °C 7.1: water; sodium hydroxide / toluene / 0.5 h / 20 °C 7.2: 0.5 h / 15 - 25 °C View Scheme |
C11H17N3O6
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: toluene-4-sulfonic acid; acetic acid / 2 h / 77 - 80 °C / Industrial scale 2.1: trichlorophosphate; triethylamine hydrochloride / 4 h / 85 °C 3.1: triethylamine / 2 h / 80 °C 4.1: potassium fluoride / dimethyl sulfoxide / 4 h / 90 °C 5.1: sodium hydrogencarbonate; water / 4 h / 100 °C 5.2: 1.17 h / 20 °C 6.1: water; sodium hydroxide / toluene / 0.5 h / 20 °C 6.2: 0.5 h / 15 - 25 °C View Scheme |
C7H5N3O4
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: trichlorophosphate; triethylamine hydrochloride / 4 h / 85 °C 2.1: triethylamine / 2 h / 80 °C 3.1: potassium fluoride / dimethyl sulfoxide / 4 h / 90 °C 4.1: sodium hydrogencarbonate; water / 4 h / 100 °C 4.2: 1.17 h / 20 °C 5.1: water; sodium hydroxide / toluene / 0.5 h / 20 °C 5.2: 0.5 h / 15 - 25 °C View Scheme |
methyl-5-chloroisoxazolo[4,5-b]pyrazine-3-carboxylate
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: triethylamine / 2 h / 80 °C 2.1: potassium fluoride / dimethyl sulfoxide / 4 h / 90 °C 3.1: sodium hydrogencarbonate; water / 4 h / 100 °C 3.2: 1.17 h / 20 °C 4.1: water; sodium hydroxide / toluene / 0.5 h / 20 °C 4.2: 0.5 h / 15 - 25 °C View Scheme |
2-pyrazine carbonitrile
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: acetic acid; dihydrogen peroxide / 22 h / -5 - 95 °C 2.1: trichlorophosphate / 1.83 h / 50 - 70 °C 2.2: 6 h / 96 °C 3.1: potassium fluoride; tetrabutylammomium bromide / dimethyl sulfoxide / 3 h / 55 °C / Sealed tube 4.1: dihydrogen peroxide / 2 h / 27 °C 5.1: sodium hydrogencarbonate; water / 8.5 h / 50 °C View Scheme |
1,4-dioxopyrazinamide
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: trichlorophosphate / 1.83 h / 50 - 70 °C 1.2: 6 h / 96 °C 2.1: potassium fluoride; tetrabutylammomium bromide / dimethyl sulfoxide / 3 h / 55 °C / Sealed tube 3.1: dihydrogen peroxide / 2 h / 27 °C 4.1: sodium hydrogencarbonate; water / 8.5 h / 50 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: trichlorophosphate / chlorobenzene / 1.83 h / 50 - 70 °C 1.2: 8 h / 110 °C 2.1: tetrabutyl ammonium fluoride; tetrabutylammomium bromide / 3 h / 60 °C / Sealed tube 3.1: sodium acetate; water / 1,4-dioxane / 7 h / 55 °C 4.1: sulfuric acid / 4 h / 50 °C View Scheme |
3-aminopyrazinoic acid
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: sulfuric acid / 20 °C / Cooling with ice 2: N-Bromosuccinimide / acetonitrile / 20 °C 3: sulfuric acid; sodium nitrite / 2 h / -5 - 20 °C 4: ammonium hydroxide / 3 h / 20 °C 5: trichlorophosphate; N-ethyl-N,N-diisopropylamine / water / 8 h / 60 - 100 °C 6: potassium fluoride; tetrabutylammomium bromide / toluene; dimethyl sulfoxide / 3 h / 55 °C 7: dihydrogen peroxide / toluene; dimethyl sulfoxide / 2 h / 27 °C / Cooling with ice 8: sodium hydrogencarbonate; water / 8.5 h / 50 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: sulfuric acid / 48 h / Cooling with ice 2.1: N-Bromosuccinimide / acetonitrile / 24 h / 20 °C / Inert atmosphere 3.1: sulfuric acid; sodium nitrite / 2 h / -5 - 25 °C 3.2: 1.5 h 4.1: ammonium hydroxide / 3 h / 20 °C 5.1: trichlorophosphate / 0.25 h / 70 °C 5.2: 6 h / 20 - 100 °C 5.3: 1 h 6.1: potassium fluoride dihydrate; tetrabutylammomium bromide / dimethyl sulfoxide / 3 h / 50 °C 7.1: potassium carbonate; dihydrogen peroxide / dimethyl sulfoxide; water / 1.5 h / 25 °C 8.1: sodium hydrogencarbonate; water / dimethyl sulfoxide / 8 h / 50 °C View Scheme |
Methyl 3-amino-2-pyrazinecarboxylate
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: N-Bromosuccinimide / acetonitrile / 20 °C 2: sulfuric acid; sodium nitrite / 2 h / -5 - 20 °C 3: ammonium hydroxide / 3 h / 20 °C 4: trichlorophosphate; N-ethyl-N,N-diisopropylamine / water / 8 h / 60 - 100 °C 5: potassium fluoride; tetrabutylammomium bromide / toluene; dimethyl sulfoxide / 3 h / 55 °C 6: dihydrogen peroxide / toluene; dimethyl sulfoxide / 2 h / 27 °C / Cooling with ice 7: sodium hydrogencarbonate; water / 8.5 h / 50 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide / acetonitrile / 24 h / 20 °C / Inert atmosphere 2.1: sulfuric acid; sodium nitrite / 2 h / -5 - 25 °C 2.2: 1.5 h 3.1: ammonium hydroxide / 3 h / 20 °C 4.1: trichlorophosphate / 0.25 h / 70 °C 4.2: 6 h / 20 - 100 °C 4.3: 1 h 5.1: potassium fluoride dihydrate; tetrabutylammomium bromide / dimethyl sulfoxide / 3 h / 50 °C 6.1: potassium carbonate; dihydrogen peroxide / dimethyl sulfoxide; water / 1.5 h / 25 °C 7.1: sodium hydrogencarbonate; water / dimethyl sulfoxide / 8 h / 50 °C View Scheme |
methyl 3-amino-6-bromopyrazine-2-carboxylate
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: sulfuric acid; sodium nitrite / 2 h / -5 - 20 °C 2: ammonium hydroxide / 3 h / 20 °C 3: trichlorophosphate; N-ethyl-N,N-diisopropylamine / water / 8 h / 60 - 100 °C 4: potassium fluoride; tetrabutylammomium bromide / toluene; dimethyl sulfoxide / 3 h / 55 °C 5: dihydrogen peroxide / toluene; dimethyl sulfoxide / 2 h / 27 °C / Cooling with ice 6: sodium hydrogencarbonate; water / 8.5 h / 50 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: sulfuric acid; sodium nitrite / 2 h / -5 - 25 °C 1.2: 1.5 h 2.1: ammonium hydroxide / 3 h / 20 °C 3.1: trichlorophosphate / 0.25 h / 70 °C 3.2: 6 h / 20 - 100 °C 3.3: 1 h 4.1: potassium fluoride dihydrate; tetrabutylammomium bromide / dimethyl sulfoxide / 3 h / 50 °C 5.1: potassium carbonate; dihydrogen peroxide / dimethyl sulfoxide; water / 1.5 h / 25 °C 6.1: sodium hydrogencarbonate; water / dimethyl sulfoxide / 8 h / 50 °C View Scheme | |
Multi-step reaction with 5 steps 1: sulfuric acid; sodium nitrite / 0.5 h / 0 - 60 °C 2: bromine; potassium carbonate / tetrahydrofuran / 12 h / 66 °C 3: tetrabutylammomium bromide; potassium fluoride / dimethyl sulfoxide; toluene / 3 h / 80 °C 4: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 20 - 25 °C 5: ammonium carbonate View Scheme |
3-hydroxy-6-bromopyrazine-2-carboxylic acid methyl ester
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: ammonium hydroxide / 3 h / 20 °C 2: trichlorophosphate; N-ethyl-N,N-diisopropylamine / water / 8 h / 60 - 100 °C 3: potassium fluoride; tetrabutylammomium bromide / toluene; dimethyl sulfoxide / 3 h / 55 °C 4: dihydrogen peroxide / toluene; dimethyl sulfoxide / 2 h / 27 °C / Cooling with ice 5: sodium hydrogencarbonate; water / 8.5 h / 50 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: ammonium hydroxide / 3 h / 20 °C 2.1: trichlorophosphate / 0.25 h / 70 °C 2.2: 6 h / 20 - 100 °C 2.3: 1 h 3.1: potassium fluoride dihydrate; tetrabutylammomium bromide / dimethyl sulfoxide / 3 h / 50 °C 4.1: potassium carbonate; dihydrogen peroxide / dimethyl sulfoxide; water / 1.5 h / 25 °C 5.1: sodium hydrogencarbonate; water / dimethyl sulfoxide / 8 h / 50 °C View Scheme | |
Multi-step reaction with 4 steps 1: bromine; potassium carbonate / tetrahydrofuran / 12 h / 66 °C 2: tetrabutylammomium bromide; potassium fluoride / dimethyl sulfoxide; toluene / 3 h / 80 °C 3: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 20 - 25 °C 4: ammonium carbonate View Scheme |
3-amino-6-bromo-pyrazine-2-carboxylic acid
favipiravir
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: sulfuric acid / 48 h / 0 - 40 °C 2: sulfuric acid; sodium nitrite / 0.5 h / 0 - 60 °C 3: bromine; potassium carbonate / tetrahydrofuran / 12 h / 66 °C 4: tetrabutylammomium bromide; potassium fluoride / dimethyl sulfoxide; toluene / 3 h / 80 °C 5: hydrogen; palladium 10% on activated carbon / methanol / 4 h / 20 - 25 °C 6: ammonium carbonate View Scheme |
favipiravir
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 60 - 65℃; for 0.166667h; Mitsunobu Displacement; Inert atmosphere; | 90% |
diethyl 2-((2-cyanoethyl)(2-hydroxyethyl)amino)ethylphosphonate
favipiravir
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 60 - 65℃; for 0.166667h; Mitsunobu Displacement; Inert atmosphere; Overall yield = 93 %; | A 23% B 70% |
tetraethyl 2,2'-(2-hydroxyethylazanediyl)bis(ethane-2,1-diyl)diphosphonate
favipiravir
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 60 - 65℃; for 0.166667h; Solvent; Temperature; Time; Mitsunobu Displacement; Inert atmosphere; Overall yield = 94 %; | A 39% B 55% |
favipiravir
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 60 - 65℃; for 0.166667h; Mitsunobu Displacement; Inert atmosphere; | 51% |
diethyl 2-((2-hydroxyethyl)(2-(trityloxy)ethyl)amino)ethylphosphonate
favipiravir
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 60 - 65℃; for 0.166667h; Mitsunobu Displacement; Inert atmosphere; Overall yield = 73 %; | A 49% B 24% |
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate
favipiravir
Conditions | Yield |
---|---|
Stage #1: favipiravir With sodium hydride In N,N-dimethyl-formamide for 1h; Inert atmosphere; Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; | 36% |
[2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,3-oxathiolan-5-yl] acetate
favipiravir
Conditions | Yield |
---|---|
Stage #1: favipiravir With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 20℃; for 1.5h; Inert atmosphere; Cooling with ice; Stage #2: [2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,3-oxathiolan-5-yl] acetate With tin(IV) chloride In acetonitrile at 20℃; for 0.333333h; Inert atmosphere; Cooling with ice; | A 30.8% B 11.8% |
favipiravir
Conditions | Yield |
---|---|
Stage #1: favipiravir With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 20℃; for 1.5h; Inert atmosphere; Cooling with ice; Stage #2: 2-tert-butyldiphenylsilyloxymethyl-4-acetyl-1,3-oxathiolane With tin(IV) chloride In acetonitrile at 20℃; for 0.333333h; Inert atmosphere; Cooling with ice; | A 12.7% B 27% |
Conditions | Yield |
---|---|
Stage #1: favipiravir With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h; Stage #2: ((3-((methylsulfonyl)oxy)cyclobutyl)methyl)benzoate In N,N-dimethyl-formamide; mineral oil at 130℃; for 25h; | 26% |
N,O-bis-(trimethylsilyl)-acetamide
favipiravir
Conditions | Yield |
---|---|
In acetonitrile at 0 - 20℃; for 1.5h; |
favipiravir
6-fluoro-3-hydroxy-2-pyrazinecarboxamide monosodium salt
Conditions | Yield |
---|---|
With sodium hydroxide In water pH=7; Reagent/catalyst; Solvent; pH-value; Temperature; |
1-deoxy-1-(methylamino)-D-glucitol
favipiravir
6-fluoro-3-hydroxy-2-pyrazinecarboxamide meglumine salt
Conditions | Yield |
---|---|
In water Concentration; Temperature; |
The 6-Fluoro-3-hydroxypyrazine-2-carboxamide, with the CAS registry number 259793-96-9, is also known as 2-Pyrazinecarboxamide, 6-fluoro-3-hydroxy-. It belongs to the product categories of Amide; Halide. This chemical's molecular formula is C5H4FN3O2 and formula weight is 157.10. What's more, both its IUPAC name and systematic name are the same which is called 5-Fluoro-2-oxo-1H-pyrazine-3-carboxamide.
Physical properties about this chemical are: (1)ACD/LogP: -1.74; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.57; (4)ACD/BCF (pH 5.5): 1.41; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 38.74; (7)ACD/KOC (pH 7.4): 1.29; (8)#H bond acceptors: 5; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 52.98 Å2; (12)Index of Refraction: 1.662; (13)Molar Refractivity: 32.63 cm3; (14)Molar Volume: 88 cm3; (15)Surface Tension: 65.6 dyne/cm; (16)Density: 1.78 g/cm3; (17)Flash Point: 288 °C; (18)Enthalpy of Vaporization: 86.43 kJ/mol; (19)Boiling Point: 552.6 °C at 760 mmHg; (20)Vapour Pressure: 8.06E-13 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=C(N=C(C(=O)N1)C(=O)N)F
(2)InChI: InChI=1S/C5H4FN3O2/c6-2-1-8-5(11)3(9-2)4(7)10/h1H,(H2,7,10)(H,8,11)
(3)InChIKey: ZCGNOVWYSGBHAU-UHFFFAOYSA-N
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