Sodium Bicarbonate → HCID 22141297, compound

Participants

Reaction Steps

To a solution of (E)-3-(3-methyl-2-thienyl)-2-propenoic acid (200 mg, 1.00 mmol) in N,N-dimethylformamide (20 ml) was added 1-hydroxybenzotriazole monohydrate (212 mg, 1.39 mmol) and 1-(3-dimethylarninopropyl)-3-ethylcarbodiimide hydrochloride (352 mg, 1.84 mmol). After stirring at room temperature for 10 min, the mixture was treated with the hydrochloride salt of N-[3-(6-methyl-3-azabicyclo[3.1.0]hex-6-yl)phenyl]methanesulfonamide (Preparation 53, 414 mg, 1.36 mmol) and sodium hydrogen carbonate (225 mg, 2.68 mmol). The reaction mixture was stirred at room temperature for 7 d and then concentrated in vacuo. Attempted partition between water (15 ml) and ethyl acetate (20 ml) produced a buff solid which was collected by filtration. Sonication for 5 min at room temperature in dichloromethane (5 ml) followed by filtration afforded the title compound as an off-white solid (280 mg, 67%).

Provenance & Evidence