Dimethylformamide → HCID 23090411, compound

Participants

Reaction Steps

To a solution of 1-[1-(6-chloro-3-pyridyl)-5-phenylpyrazole-3-carbonyl]-4-methylpiperazine (300 mg) obtained in Example 110 in N,N-dimethylformamide (1.5 mL), 40% methylamine-methanol solution (0.6 mL) was added. The mixture was stirred at 85>C for 3 days in a sealed tube, and then cooled in air. The reaction mixture was partitioned between 1N aqueous sodium hydroxide (30 mL) and ethyl acetate. The organic layer was sequentially washed with water, saturated aqueous sodium hydrogencarbonate, and water, and then dried over magnesium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure, and the residue was dissolved in dimethyl sulfoxide (1 mL). The solution was purified through preparative high-performance liquid chromatography (eluent: water acetonitrile), followed by recrystallization from ether-hexane, to thereby give the title compound (11.7 mg, 4%).

Provenance & Evidence