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High Quality 99% Favipiravir 259793-96-9 GMP Manufacturer
Cas No: 259793-96-9
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6-FLUORO-3-OXO-3,4-DIHYDROPYRAZINE-2-CARBOXAMIDE
Cas No: 259793-96-9
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier

259793-96-9 Usage

Mode of Action

Favipiravir inhibits the RNA-dependent RNA polymerase (RdRp) — an enzyme that allows the coronavirus to replicate inside host cells.Inside the cells, favipiravir is converted to favipiravir ribofuranosyl-5′-triphosphate (favipiravir-RTP) by host cells. This molecule then blocks the RdRp enzyme of SARS-CoV-2, the virus that causes Covid-19.According to a statement by Glenmark, favipiravir works only during the earlier stages of the disease, when the viral replication is higher, but the body's immune response has not gone into overdrive. Metabolism of favipiravir to its triphosphate form occurs in an extracellular environment in a concentration-dependent manner. The vRNA polymerase mistakenly recognizes favipiravir-RTP as a purine nucleotide. This favipiravir-RTP is misincorporated in nascent vRNA, or it may act by binding to conserved polymerase domains, preventing incorporation of nucleotides for vRNA replication and transcription (Jin et al., 2013).

History

Favipiravir is a broad-spectrum antiviral drug that was cleared by the Drugs Controller General of India (DCGI) last week for “emergency restricted” use among Covid-19 patients. Glenmark will sell the generic favipiravir under the brand name FabiFlu. Favipiravir was originally developed in the late 1990s by a company that was later purchased by the Japanese firm Fujifilm as part of its transition from the photo business to healthcare. After being tested against a range of viruses, the drug was approved in Japan in 2014 for emergency use against flu epidemics or to treat new strains of influenza.

A Potential Antiviral for COVID-19?

Currently, there is not any specific effective antiviral treatment for COVID-19. Although most of the COVID-19 patients have mild or moderate courses, up to 5%–10% can have severe, potentially life threatening course, there is an urgent need for effective drugs. Optimized supportive care remains the mainstay of therapy. There have been more than 300 clinical trials going on, various antiviral and immunomodulating agents are in various stages of evaluation for COVID-19 in those trials and some of them will be published in the next couple of months. Despite the urgent need to find an effective antiviral treatment for COVID-19 through randomized controlled studies, certain agents are being used all over the world based on either in-vitro or extrapolated evidence or observational studies. The most frequently used agents both in Turkey and all over the world including chloroquine, hydroxychloroquine, lopinavir/ritonavir, favipiravir and remdesivir will be reviewed here .Nitazoxanide and ivermectin were also included in this review as they have recently been reported to have an activity against SARS-CoV-2 in vitro and are licensed for the treatment of some other human infections.

259793-96-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-fluoro-2-oxo-1H-pyrazine-3-carboxamide

1.2 Other means of identification

Product number -
Other names 6-FLUORO-3-HYDROXYPYRAZINE-2-CARBOXAMIDE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:259793-96-9 SDS

259793-96-9Synthetic route

6-fluoro-3-hydroxy-2-cyanopyrazine
356783-31-8

6-fluoro-3-hydroxy-2-cyanopyrazine

favipiravir
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

C6H5FN2O3

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
With ammonium carbonate Reagent/catalyst;92.3%
3,6-difluoro-2-pyrazinecarboxamide
356783-29-4

3,6-difluoro-2-pyrazinecarboxamide

favipiravir
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%
3,6-difluoropyrazine-2-carbonitrile
356783-28-3

3,6-difluoropyrazine-2-carbonitrile

favipiravir
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
dicyclohexylamine salt
1137606-74-6

dicyclohexylamine salt

favipiravir
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

C12H10FN3O2

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
With ammonia; sodium In tetrahydrofuran at -70 - -65℃;72%
2-hydroxypyrazine-3-carboxamide
55321-99-8

2-hydroxypyrazine-3-carboxamide

favipiravir
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

3-hydroxy-6-bromopyrazine-2-carboxamide

favipiravir
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

6-fluoro-3-methoxy-2-pyrazinecarboxamide

favipiravir
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
methyl 6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarboxylate
356783-27-2

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

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
With sodium bicarbonate; sodium chloride; ammonia In methanol; water; ethyl acetate
6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarbonitrile
356783-31-8

6-fluoro-3-oxo-3,4-dihydro-2-pyrazinecarbonitrile

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
With sodium hydroxide; sulfuric acid; dihydrogen peroxide In water
3-amino-6-fluoro-2-pyrazinecarboxamide
356783-42-1

3-amino-6-fluoro-2-pyrazinecarboxamide

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
356783-16-9

3,6-dichloropyrazine-2-carbonitrile

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
1374986-08-9

C9H8ClN3O3

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
1374986-19-2

C9H8FN3O3

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
1374986-28-3

C9H10N4O6S

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
1374986-36-3

C9H12N2O4

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
1374986-38-5

C9H11N3O5

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
C11H15N2O6(1-)*K(1+)

C11H15N2O6(1-)*K(1+)

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
1374986-03-4

C11H17N3O6

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
1374986-04-5

C7H5N3O4

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
1374986-05-6

methyl-5-chloroisoxazolo[4,5-b]pyrazine-3-carboxylate

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
19847-12-2

2-pyrazine carbonitrile

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
18960-19-5

1,4-dioxopyrazinamide

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
5424-01-1

3-aminopyrazinoic acid

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
16298-03-6

Methyl 3-amino-2-pyrazinecarboxylate

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
6966-01-4

methyl 3-amino-6-bromopyrazine-2-carboxylate

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
21874-61-3

3-hydroxy-6-bromopyrazine-2-carboxylic acid methyl ester

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
486424-37-7

3-amino-6-bromo-pyrazine-2-carboxylic acid

favipiravir
259793-96-9

favipiravir

Conditions
ConditionsYield
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
tetraethyl {[(2-hydroxypropane-1,3-diyl)bis(oxy)]bis(ethylene)}bis(phosphonate)

tetraethyl {[(2-hydroxypropane-1,3-diyl)bis(oxy)]bis(ethylene)}bis(phosphonate)

favipiravir
259793-96-9

favipiravir

tetraethyl 5-((3-carbamoyl-5-fluoropyrazin-2-yl)oxy)-3,7-dioxanonane-1,9-diphosphonate

tetraethyl 5-((3-carbamoyl-5-fluoropyrazin-2-yl)oxy)-3,7-dioxanonane-1,9-diphosphonate

Conditions
ConditionsYield
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
1383381-61-0

diethyl 2-((2-cyanoethyl)(2-hydroxyethyl)amino)ethylphosphonate

favipiravir
259793-96-9

favipiravir

A

diethyl 3-(2-(3-carbamoyl-5-fluoro-2-oxopyrazin-1-yl)ethyl)-5-cyano-3-azapentanephosphonate

diethyl 3-(2-(3-carbamoyl-5-fluoro-2-oxopyrazin-1-yl)ethyl)-5-cyano-3-azapentanephosphonate

B

diethyl 3-(2-((3-carbamoyl-5-fluoropyrazin-2-yl)oxy)ethyl)-5-cyano-3-azapentanephosphonate

diethyl 3-(2-((3-carbamoyl-5-fluoropyrazin-2-yl)oxy)ethyl)-5-cyano-3-azapentanephosphonate

Conditions
ConditionsYield
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
1332338-67-6

tetraethyl 2,2'-(2-hydroxyethylazanediyl)bis(ethane-2,1-diyl)diphosphonate

favipiravir
259793-96-9

favipiravir

A

tetraethyl 3-(2-(3-carbamoyl-5-fluoro-2-oxopyrazin-1-yl)ethyl)-3-azapentane-1,5-diphosphonate

tetraethyl 3-(2-(3-carbamoyl-5-fluoro-2-oxopyrazin-1-yl)ethyl)-3-azapentane-1,5-diphosphonate

B

tetraethyl 3-(2-((3-carbamoyl-5-fluoropyrazin-2-yl)oxy)ethyl)-3-azapentane-1,5-diphosphonate

tetraethyl 3-(2-((3-carbamoyl-5-fluoropyrazin-2-yl)oxy)ethyl)-3-azapentane-1,5-diphosphonate

Conditions
ConditionsYield
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%
diethyl [2-(2-hydroxyethoxy)ethyl]phosphonate

diethyl [2-(2-hydroxyethoxy)ethyl]phosphonate

favipiravir
259793-96-9

favipiravir

diethyl 5-((3-carbamoyl-5-fluoropyrazin-2-yl)oxy)-3-oxapentanephosphonate

diethyl 5-((3-carbamoyl-5-fluoropyrazin-2-yl)oxy)-3-oxapentanephosphonate

Conditions
ConditionsYield
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
1383381-63-2

diethyl 2-((2-hydroxyethyl)(2-(trityloxy)ethyl)amino)ethylphosphonate

favipiravir
259793-96-9

favipiravir

A

diethyl 3-(2-((3-carbamoyl-5-fluoropyrazin-2-yl)oxy)ethyl)-5-trityloxy-3-azapentanephosphonate

diethyl 3-(2-((3-carbamoyl-5-fluoropyrazin-2-yl)oxy)ethyl)-5-trityloxy-3-azapentanephosphonate

B

diethyl 3-(2-(3-carbamoyl-5-fluoro-2-oxopyrazin-1-yl)ethyl)-5-trityloxy-3-azapentanephosphonate

diethyl 3-(2-(3-carbamoyl-5-fluoro-2-oxopyrazin-1-yl)ethyl)-5-trityloxy-3-azapentanephosphonate

Conditions
ConditionsYield
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
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

favipiravir
259793-96-9

favipiravir

dibenzyl (3-carbamoyl-5-fluoropyrazin-2-yl) phosphate

dibenzyl (3-carbamoyl-5-fluoropyrazin-2-yl) phosphate

Conditions
ConditionsYield
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
139757-72-5

[2-[[tert-butyl(diphenyl)silyl]oxymethyl]-1,3-oxathiolan-5-yl] acetate

favipiravir
259793-96-9

favipiravir

trans-4-(2'-(tert-butyl-diphenylsilyloxy)methyl-1',3'-oxathiolan-5'-yl)-6-fluoro-3,4-dihydro-3-oxo-2-pyrazine-carboxamide

trans-4-(2'-(tert-butyl-diphenylsilyloxy)methyl-1',3'-oxathiolan-5'-yl)-6-fluoro-3,4-dihydro-3-oxo-2-pyrazine-carboxamide

cis-4-(2'-(tert-butyl-diphenylsilyloxy)methyl-1',3'-oxathiolan-5'-yl)-6-fluoro-3,4-dihydro-3-oxo-2-pyrazine-carboxamide

cis-4-(2'-(tert-butyl-diphenylsilyloxy)methyl-1',3'-oxathiolan-5'-yl)-6-fluoro-3,4-dihydro-3-oxo-2-pyrazine-carboxamide

Conditions
ConditionsYield
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%
2-tert-butyldiphenylsilyloxymethyl-4-acetyl-1,3-oxathiolane

2-tert-butyldiphenylsilyloxymethyl-4-acetyl-1,3-oxathiolane

favipiravir
259793-96-9

favipiravir

cis-4-(2'-(t-butyl-diphenylsilyloxy)methyl-1',3'-oxathiolan-4'-yl)-6-fluoro-3,4-dihydro-3-oxo-2-pyrazine-carboxamide

cis-4-(2'-(t-butyl-diphenylsilyloxy)methyl-1',3'-oxathiolan-4'-yl)-6-fluoro-3,4-dihydro-3-oxo-2-pyrazine-carboxamide

trans-4-(2'-(t-butyl-diphenylsilyloxy)methyl-1',3'-oxathiolan-4'-yl)-6-fluoro-3,4-dihydro-3-oxo-2-pyrazinecarboxamide

trans-4-(2'-(t-butyl-diphenylsilyloxy)methyl-1',3'-oxathiolan-4'-yl)-6-fluoro-3,4-dihydro-3-oxo-2-pyrazinecarboxamide

Conditions
ConditionsYield
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%
((3-((methylsulfonyl)oxy)cyclobutyl)methyl)benzoate
929911-63-7

((3-((methylsulfonyl)oxy)cyclobutyl)methyl)benzoate

favipiravir
259793-96-9

favipiravir

C17H16FN3O4

C17H16FN3O4

Conditions
ConditionsYield
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
10416-59-8

N,O-bis-(trimethylsilyl)-acetamide

favipiravir
259793-96-9

favipiravir

6-fluoro-3-((trimethylsilyl)oxy)pyrazine-2-carboxamide

6-fluoro-3-((trimethylsilyl)oxy)pyrazine-2-carboxamide

Conditions
ConditionsYield
In acetonitrile at 0 - 20℃; for 1.5h;
favipiravir
259793-96-9

favipiravir

6-fluoro-3-hydroxy-2-pyrazinecarboxamide monosodium salt
1366418-99-6

6-fluoro-3-hydroxy-2-pyrazinecarboxamide monosodium salt

Conditions
ConditionsYield
With sodium hydroxide In water pH=7; Reagent/catalyst; Solvent; pH-value; Temperature;
1-deoxy-1-(methylamino)-D-glucitol
6284-40-8

1-deoxy-1-(methylamino)-D-glucitol

favipiravir
259793-96-9

favipiravir

6-fluoro-3-hydroxy-2-pyrazinecarboxamide meglumine salt
1370365-08-4

6-fluoro-3-hydroxy-2-pyrazinecarboxamide meglumine salt

Conditions
ConditionsYield
In water Concentration; Temperature;

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