Triethylamine → N-(4-((2-(cyclobutanecarboxamido)pyridin-4-yl)oxy)-3-fluorophenyl)-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)-3-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (100 mg, 0.231 mmol) in THF/DMF (15 mL/0.5 mL) was added Et3N (0.058 mL, 0.462 mmol). The suspension was cooled to 0° C., then a solution of cyclobutanecarbonyl chloride (30 mg, 0.254 mmol) in THF (5 mL) was added to the mixture drop wise over 1 hour. The reaction was stirred at rt for 2 hours, then diluted with EtOAc (20 mL). The 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/v)=100/20/1) to give the title compound as a white solid (51 mg, 44%).

Provenance & Evidence