Water → HCID 58181320, compound

Participants

Reaction Steps

To a suspension of (3-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)acetic acid (213.4 mg, 0.581 mmol) in anhydrous N,N-dimethylformamide (3 ml) was added 1,1′-carbonyldiimidazole (188.9 mg, 1.165 mmol), and the mixture was stirred at room temperature for 1.5 hrs. tert-Butyl carbazate (460.3 mg, 3.483 mmol) was added, and the mixture was stirred at room temperature for 14 hrs. Water and ethyl acetate were added to the reaction mixture, and the mixture was stirred, stood still and partitioned. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified 3 times by silica gel column chromatography (ethyl acetate→methanol: dichloromethane=1:15, methanol:dichloromethane=1:20, methanol:dichloromethane=1:20) to give tert-butyl 2-[(3-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}phenyl)acetyl]hydrazinecarboxylate (219.4 mg, yield 78.4%) as a white solid.

Provenance & Evidence