Morpholine → HCID 73053699, compound

Participants

Reaction Steps

To a suspension of N-(5-((2-aminopyridin-4-yl)oxy)pyridin-2-yl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (171 mg, 0.41 mmol) and Et3N (0.17 mL, 1.23 mmol) in THF (8.0 mL) was added phenyl carbonochloridate (0.15 mL, 1.23 mmol). The mixture was stirred at rt for 2 hours, then morpholine (0.21 mL, 2.46 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 were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (MeOH/EtOAc (v/v)=1/50) and TLC (MeOH/EtOAc (v/v)=1/30) to give the title compound as a pale yellow solid (40 mg, 18%).

Provenance & Evidence