Methanol → 3-(3-Benzoyl-3-azabicyclo[3.1.0]hexane-6-carboxamido)methyl-5-isobutyl-1-phenyl-1H-pyrazole

Participants

Reaction Steps

The 6-((5-isobutyl-1-phenyl-1H-pyrazole-3-yl)methylcarbamoyl)-3-azabicyclo[3.1.0]hexane hydrochloride (367 mg, 0.979 mmol) prepared in Example 11 was dissolved in 4.9 mL of methylene chloride and triethylamine (273 μL, 1.96 mmol) was added dropwise at 0° C. After stirring for 5 minutes, benzoyl chloride (125 μL, 1.08 mmol) was added dropwise. 10 minutes later, after stirring at room temperature for 3 hours, the completion of the reaction was confirmed by TLC (CH2Cl2:MeOH=20:1). After the reaction was completed, the reaction mixture was extracted with methylene chloride after adding water, 1 N HCl and saturated sodium bicarbonate. The organic layer was dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and separated by column chromatography (CH2Cl2:MeOH=20:1) to obtain 360 mg (83.2%) of the target compound.

Provenance & Evidence