Triethylamine → N-(4-((2-(cyclopentanecarboxamido)pyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of N-(4-((2-aminopyridin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (100 mg, 0.241 mmol) in THF/DMF (20 mL/1 mL) was added Et3N (0.06 mL, 0.481 mmol). The suspension was cooled to 0° C., a solution of cyclopentanecarbonyl chloride (64.0 mg, 0.481 mmol) in THF (5 mL) was added to the reaction mixture drop wise over 2 hours. The reaction was stirred at rt for 1.5 hours, then diluted with EtOAc (25 mL). The resulted mixture was washed with water (25 mL×3), followed by washing with brine (25 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (DCM/EtOAc/MeOH (v/v)=80/15/1) to give the title compound as a white solid (39 mg, 32%).

Provenance & Evidence