Water → tert-butyl 4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-4-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)piperidine-1-carboxylate

Participants

Reaction Steps

To a suspension of 378 mg of tert-butyl 4-((6-((1-tert-butyl-1H-pyrazol-5-yl)amino)pyridin-2-yl)methyl)-4-(hydrazinocarbonyl)piperidine-1-carboxylate in 10 ml of tetrahydrofuran was added 130 mg of 1,1′-carbonyldiimidazole at room temperature. After stirring at room temperature for 3 hours, 100 mg of 1,1′-carbonyldiimidazole was added at room temperature, followed by stirring at room temperature for 5 days. To the reaction mixture was added 10 ml of saturated aqueous sodium bicarbonate solution, followed by stirring the reaction mixture at room temperature for 30 minutes. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=20/1−1/2) to give the title compound as a pale yellow oil.

Provenance & Evidence