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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence