Morpholine → HCID 73053700, compound

Participants

Reaction Steps

To a suspension of N-(4-((2-aminopyridin-4-yl)oxy)-3-chlorophenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (135 mg, 0.3 mmol) in THF (3 mL) was added Et3N (0.080 mL, 0.6 mmol), followed by adding phenyl carbonochloridate (0.075 mL, 0.6 mmol) dropwise. The reaction mixture was stirred at rt for 2 hours, then morpholine (0.250 mL, 3.0 mmol) was added. The reaction mixture was stirred at rt for 22 hours, quenched with saturated NH4Cl aqueous (20 mL) and CH2Cl2 (20 mL). The resulted mixture was stirred at rt for 10 minutes, and extracted with CH2Cl2 (20 mL×3). The combined organic phases were washed with brine (20 mL×3), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/PE (v/v)=6/1) to give the title compound as a beige solid (43 mg, 25.4%).

Provenance & Evidence