Water → Tert-butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)benzyl]carbamoyl}hydrazinecarboxylate

Temperatur

50 °C

To a suspension of 2-(acetylamino)-1,3-thiazole-4-carboxylic acid (558.6 mg, 3.000 mmol) in anhydrous tetrahydrofuran (10 ml) were added 1,1′-carbonyldiimidazole (535.2 mg, 3.301 mmol) and anhydrous tetrahydrofuran (10 ml), and the mixture was stirred at 50° C. for 2 hr. tert-Butyl 2-[(4-aminobenzyl)carbamoyl]hydrazinecarboxylate (841.0 mg, 3.000 mmol) was added, and the mixture was stirred for 24 hr. To a solution of 2-(acetylamino)-1,3-thiazole-4-carboxylic acid (280.2 mg, 1.505 mmol) in anhydrous N,N-dimethylformamide (5 ml) was added 1,1′-carbonyldiimidazole (243.2 mg, 1.500 mmol), and the mixture was stirred at 50° C. for 30 min. This solution was added to the mixture obtained above, and the mixture was stirred at 50° C. for 3 hr, and at room temperature for 65 hr. Water and ethyl acetate were added to the reaction mixture and the mixture was stirred. The precipitated solid was filtered, washed with ethyl acetate, and dried under reduced pressure to give tert-butyl 2-{[4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)benzyl]carbamoyl}hydrazinecarboxylate (1.223 g, 2.728 mmol, yield 90.9%) as a white solid.

1. stirringthe mixture was stirred for 24 hr
2. stirringthe mixture was stirred at 50° C. for 30 min
3. additionThis solution was added to the mixture
4. customobtained above, and the mixture
5. stirringwas stirred at 50° C. for 3 hr
6. waitat room temperature for 65 hr
7. stirringthe mixture was stirred
8. filtrationThe precipitated solid was filtered
9. washwashed with ethyl acetate
10. customdried under reduced pressure

ORD-Eintrag

ord-9f44db9c26654cebb26c2ea592e61eab

Quelldatensatz

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08507690B2