反应详情

Dicyclohexylcarbodiimide (2.3 g) was added slowly to a suspension of nicotinic acid N-oxide (1.5 g) in N,N-dimethylformamide (40 ml) with cooling on an ice bath and the mixture was stirred for 15 minutes with cooling on an ice bath. To the mixture 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (2.0 g) was added with cooling on an ice bath. The mixture was stirred for an hour with cooling on an ice bath and then stirred for 41 hours at room temperature. The solvent was removed under reduced pressure and the residue was suspended in water. 6N-Hydrochloric acid solution was added to the suspension and the resulting precipitate was removed by filtration. The solvent was removed under reduced pressure and the residue was dissolved in methanol. The insoluble material was removed by filtration and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column eluting with a mixture of chloroform and methanol (10:1, V/V). Recrystallization from a mixture of methanol, dioxane and diisopropyl ether afforded 2-(diaminomethyleneamino)-4-[5-(1-oxonicotinoylaminomethyl)furan-2-yl]thiazole (0.30 g).

1. temperaturewith cooling on an ice bath
2. temperaturewith cooling on an ice bath
3. temperaturewith cooling on an ice bath
4. stirringThe mixture was stirred for an hour
5. temperaturewith cooling on an ice bath
6. stirringstirred for 41 hours at room temperature
7. customThe solvent was removed under reduced pressure
8. addition6N-Hydrochloric acid solution was added to the suspension
9. customthe resulting precipitate was removed by filtration
10. customThe solvent was removed under reduced pressure
11. dissolutionthe residue was dissolved in methanol
12. customThe insoluble material was removed by filtration
13. customthe solvent was removed under reduced pressure
14. customThe residue was chromatographed on a silica gel column
15. washeluting with a mixture of chloroform and methanol (10:1, V/V)
16. customRecrystallization
17. additionfrom a mixture of methanol, dioxane and diisopropyl ether