Diisopropylethylamine → HCID 86686914, compound

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of (6-fluoro-3-methyl-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester trifluoroacetate salt (which may be prepared as described above; 102 mg, 0.237 mmol) and N,N-diisopropylethylamine (124 μL, 0.711 mmol) in methylene chloride (6.0 mL) was added (4-chloro-phenyl)-methanesulfonyl chloride (106.7 mg, 0.474 mmol). The reaction mixture was stirred at 0° C. for 10 minutes, then it was warmed to room temperature and stirred at room temperature for four hours. The reaction mixture was diluted with water (25 mL). The resulting mixture was extracted with ethyl acetate (2×25 mL). The organic phase was dried over MgSO4, filtered, and concentrated. Silica gel chromatography (20-25% ethyl acetate in hexanes) provided {4-[1-(4-chloro-phenylmethanesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (28.5 mg, 24%) as a colorless film. MS cald. For C26H28ClFNO4S [(M+H)+]: 504, obsd. 504.2.

Provenance & Evidence