Morpholine → N-(4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2,5-difluorophenoxy)pyridin-2-yl)morpholine-4-carboxamide

Participants

Reaction Steps

To a suspension of N-(4-((2-aminopyridin-4-yl)oxy)-2,5-difluorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (250 mg, 0.56 mmol) and Et3N (0.25 mL, 1.68 mmol) in THF (10.0 mL) was added phenyl carbonochloridate (0.25 mL, 1.68 mmol). The mixture was stirred at rt for 2 hours, then morpholine (0.35 mL, 3.46 mmol) was added. The reaction mixture was stirred rt for 24 hours and partitioned between aq NH4Cl (40 mL) and DCM (40 mL). The organic phase was separated and the aqueous phase was extracted with DCM (40 mL×3). The combined organic phases was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/PE (v/v)=4/1) to give the title compound as a white solid (70 mg, 21%).

Provenance & Evidence