1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(3-fluoro-4-((7-hydroxyquinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(4-amino-2-fluorophenoxy)quinolin-7-ol (10 g, 37.0 mmol), 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (10 g, 44.4 mmol), HOAT (0.5 g, 3.7 mmol) in DMF (50 mL) and toluene (30 mL) was added EDCI (8.5 g, 44.4 mmol). The reaction was stirred at 45° C. overnight, then diluted with water (100 mL) and continued to stir at room temperature for 2 hours. The solid was collected through filtration, washed with a mixture of 95% EtOH (50 mL) and DCM (25 mL), and then treated with 3 M hydrochloric acid (10.5 mL). The resulted solid was collected and was recrystallized in a mixture of 95% EtOH and H2O (90 mL, EtOH/H2O=5:1, v/v) to give the title compound as a white solid (11.7 g, 60.8%).

Provenance & Evidence