(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acid → HCID 22141171, compound

Participants

Reaction Steps

To a solution of 4-(trifluoromethyl)phenyl acetic acid (63 mg, 0.31 mmol) in N,N-dimethylformamide (6.5 ml) was added 1-hydroxybenzotriazole monohydrate (50 mg, 0.33 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (85 mg, 0.44 mmol). After stirring at room temperature for 5 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, 100 mg, 0.33 mmol) and sodium hydrogen carbonate (28 mg, 0.34 mmol). The reaction mixture was stirred at room temperature for 18 h before concentrating in vacua. Water (10 ml) was added and the reaction mixture was extracted with ethyl acetate (2×15 ml). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to give a light brown oil. The residue was purified by chromatography using a Sep-Pak™ cartridge packed with silica gel (5 g) eluting with dichloromethane:ethanol:0.88 ammonia (200:8:1) to afford the title compound as a glassy oil (70 mg, 47%).

Provenance & Evidence