GB1082060A - Aminopyrazinoic acids and their esters - Google Patents
Aminopyrazinoic acids and their estersInfo
- Publication number
- GB1082060A GB1082060A GB4071464A GB4071464A GB1082060A GB 1082060 A GB1082060 A GB 1082060A GB 4071464 A GB4071464 A GB 4071464A GB 4071464 A GB4071464 A GB 4071464A GB 1082060 A GB1082060 A GB 1082060A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- methyl
- guanidine
- alkyl
- chlorine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:1082060/C2/1> in which R1 is a chlorine atom, a C1-C5 alkyl radical or a phenyl radical; R2 is a chlorine atom, a C1-C5 alkyl, or a cycloalkyl or phenyl radical; at least one of R1 and R2 being chlorine, and R3 is a hydrogen atom or a C1-C5 alkyl radical. The esters of the above formula may be prepared by reacting a 3-amino-pyrazinoic acid compound of formula <FORM:1082060/C2/2> in which R4 is a hydrogen atom, a C1-C5 alkyl radical or a phenyl radical; R5 is a hydrogen, chlorine, bromine or iodine atom or a C1-C5 alkyl or a cycloalkyl or phenyl radical, at least one of R4 and R5 being hydrogen or halogen, and R6 is a C1-C5 alkyl radical, with sulphuryl chloride. The esters may be hydrolysed to give the corresponding acids. The starting 3-amino-pyrazinoic acid compounds having a hydrocarbon group in the 6-position may be prepared from the corresponding 6-substituted-3-amino pyrazinamides by heating with sodium hydroxide solution, acidifying the sodium salt so obtained to give the free acid and converting this to an ester e.g. by reacting with methanol. Starting materials having a halogen in the 6-position, for example methyl-3-amino-6-chloropyrazinoate and methyl-3-amino-6-iodopyrazinoate are made by the direct halogenation of methyl - 3 - aminopyrazinoate. 3 - Amino - 6-cyclohexylpyrazinamide which is used for producing the starting material 3-amino-6-cyclohexylpyrazinoic acid is obtained by reacting aminomalonamidamidine dihydrochloride with cyclohexyl glyoxal. The new compounds may be used as intermediates in the formation of guanidine derivatives. For example, metallic sodium dissolved in propanol is treated with guanidine hydrochloride, methyl 1-3-amino-5,6-dichloropyrazinoate is added to the resulting guanidine solution and (3 - amino - 5,6 - dichloropyrazinoyl)-guanidine hydrochloride is separated; this compound may be further reacted with dimethylamine to give (3 - amino - 5 - dimethylamino - 6 - chloropyrazinoyl) guanidine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4071464A GB1082060A (en) | 1964-10-06 | 1964-10-06 | Aminopyrazinoic acids and their esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4071464A GB1082060A (en) | 1964-10-06 | 1964-10-06 | Aminopyrazinoic acids and their esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1082060A true GB1082060A (en) | 1967-09-06 |
Family
ID=10416255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4071464A Expired GB1082060A (en) | 1964-10-06 | 1964-10-06 | Aminopyrazinoic acids and their esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1082060A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115536599A (en) * | 2022-09-26 | 2022-12-30 | 合肥利夫生物科技有限公司 | Preparation method of Favipiravir intermediate 3,6-difluoro-2-pyrazinecarbonitrile |
| CN117946013A (en) * | 2024-01-25 | 2024-04-30 | 白银康寓信生物科技有限公司 | Method for synthesizing 5, 6-dihalogen-3-aminopyrazine-2-methyl formate by one-pot method |
-
1964
- 1964-10-06 GB GB4071464A patent/GB1082060A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115536599A (en) * | 2022-09-26 | 2022-12-30 | 合肥利夫生物科技有限公司 | Preparation method of Favipiravir intermediate 3,6-difluoro-2-pyrazinecarbonitrile |
| CN117946013A (en) * | 2024-01-25 | 2024-04-30 | 白银康寓信生物科技有限公司 | Method for synthesizing 5, 6-dihalogen-3-aminopyrazine-2-methyl formate by one-pot method |
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