1,1'-Carbonyldiimidazole → Tert-butyl 2-[(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl)carbamoyl]hydrazinecarboxylate

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Reaction Steps

To a suspension of 1,1′-carbonyldiimidazole (125.2 mg, 0.792 mmol) in anhydrous tetrahydrofuran (1 ml) was added tert-butyl carbazate (102.1 mg, 0.792 mmol), and the mixture was stirred at room temperature for 1 hr. 1-(4-{2-[5-(4-Acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)methanamine (130.7 mg, 0.386 mmol) was added, and the mixture was stirred at room temperature for 4 hrs. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and aqueous sodium carbonate solution were added. The mixture was stirred, stood still and partitioned. The aqueous layer was extracted twice with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate→methanol:dichloromethane=1:20). The fraction containing the target product was concentrated and the obtained solid was suspended in a mixture of ethyl acetate (5 ml) and diisopropyl ether (10 ml), filtered and dried under reduced pressure to give tert-butyl 2-[(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl)carbamoyl]hydrazinecarboxylate (145.9 mg, yield 76.1%) as a white solid.

Provenance & Evidence