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

Participants

Reaction Steps

To a solution of N-(4-((2-aminopyridin-4-yl)oxy)-3-fluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (217 mg, 0.5 mmol) in DCM (5 mL) was added Et3N (253 mg, 2.5 mmol) and cyclopropanecarbonyl chloride (125 mg, 1.2 mmol) at 0° C. The reaction mixture was stirred at rt for 4 hours, quenched with H2O (10 mL) and extracted with DCM (50 mL×3). The combined organic phases were washed with brine (50 mL×3), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was dissolved in CH3OH (20 mL), and a solution of Na2CO3 (106 mg, 1.0 mmol) in H2O (1 mL). The resulted mixture was stirred at rt for 1 hour and concentrated in vacuo. The residue was purified by a silica gel column chromatography (pure DCM) to give the title compound as a beige solid (158 mg, 63.2%).

Provenance & Evidence