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6-Fluoro-3-hydroxypyrazine-2-carboxamide
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Name

6-Fluoro-3-hydroxypyrazine-2-carboxamide

 EINECS 1533716-785-6
CAS No. 259793-96-9 Density 1.78 g/cm3
PSA 88.84000 LogP -0.29180
Solubility N/A Melting Point N/A
Formula C5H4FN3O2 Boiling Point 552.6 °C at 760 mmHg
Molecular Weight 157.104 Flash Point 288 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 259793-96-9 (Pyrazinecarboxamide, 6-fluoro-3,4-dihydro-3-oxo- (9CI)) Hazard Symbols N/A
Synonyms

Pyrazinecarboxamide,6-fluoro-3,4-dihydro-3-oxo- (9CI);6-Fluoro-3-hydroxy-2-pyrazinecarboxamide;Favipiravir;T 705 (pharmaceutical);

Article Data 24

6-Fluoro-3-hydroxypyrazine-2-carboxamide Synthetic route

356783-31-8

6-fluoro-3-hydroxy-2-cyanopyrazine

259793-96-9

favipiravir

Conditions
ConditionsYield
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;

C6H5FN2O3

259793-96-9

favipiravir

Conditions
ConditionsYield
With ammonium carbonate Reagent/catalyst;92.3%
356783-29-4

3,6-difluoro-2-pyrazinecarboxamide

259793-96-9

favipiravir

Conditions
ConditionsYield
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%
356783-28-3

3,6-difluoropyrazine-2-carbonitrile

259793-96-9

favipiravir

Conditions
ConditionsYield
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
1137606-74-6

dicyclohexylamine salt

259793-96-9

favipiravir

Conditions
ConditionsYield
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

C12H10FN3O2

259793-96-9

favipiravir

Conditions
ConditionsYield
With ammonia; sodium In tetrahydrofuran at -70 - -65℃;72%
55321-99-8

2-hydroxypyrazine-3-carboxamide

259793-96-9

favipiravir

Conditions
ConditionsYield
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

3-hydroxy-6-bromopyrazine-2-carboxamide

259793-96-9

favipiravir

Conditions
ConditionsYield
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

6-fluoro-3-methoxy-2-pyrazinecarboxamide

259793-96-9

favipiravir

Conditions
ConditionsYield
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
356783-27-2

methyl 6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarboxylate

259793-96-9

favipiravir

Conditions
ConditionsYield
With sodium bicarbonate; sodium chloride; ammonia In methanol; water; ethyl acetate

6-Fluoro-3-hydroxypyrazine-2-carboxamide Specification

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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