Formic Acid → HCID 9993589, compound

Temperature

45 °C

A mixture of formic acid (0.47 ml) and acetic anhydride (0.87 ml) was stirred at 40-50° C. for 30 minutes. To a mixture of 4-(6-aminomethylpyridin-2-yl)-2(diaminomethyleneamino)thiazole trihydrochloride (3.0 g) and triethylamine (3.5 ml) in N,N-dimethylformamide (45 ml) was added the above mixture under ice-cooling and the mixture was stirred at ambient temperature for 5 hours. The reaction mixture was added to water and the mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract layer was washed with brine, and dried over magnesium sulfate. Evaporation of a solvent gave a residue, which was purified by column chromatography on alumina, eluting with a mixture of chloroform and methanol (9:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo. The residue was recrystallized from an aqueous methanol to give 2-(diaminomethyleneamino)-4-(6-formylaminomethylpyridin-2-yl)thiazole (0.62 g).

1. additionwas added the above mixture under ice-
2. temperaturecooling
3. stirringthe mixture was stirred at ambient temperature for 5 hours
4. extractionthe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
5. washThe extract layer was washed with brine
6. dry with materialdried over magnesium sulfate
7. customEvaporation of a solvent
8. customgave a residue, which
9. customwas purified by column chromatography on alumina
10. washeluting with a mixture of chloroform and methanol (9:1, V/V)
11. additionThe eluted fractions containing the desired product
12. customwere collected
13. customevaporated in vacuo
14. customThe residue was recrystallized from an aqueous methanol

ORD record

ord-1edf51dbf9224bce908cd868b240bb35

Source dataset

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05371097