Diisopropylethylamine → HCID 86686917, 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 (10.0 mL) was added pyrrolidine-1-sulfonyl chloride (80.4 mg, 0.474 mmol). The reaction mixture was stirred at 0° C. for 25 minutes, and then warmed to room temperature and stirred overnight. During this time period the solvent evaporated to dryness. Additional methylene chloride (10 mL) was added in the morning. The reaction mixture was diluted with water (25 mL). The resulting mixture was extracted with ethyl acetate (2×30 mL). The organic phase was dried over MgSO4, filtered, and concentrated. Silica gel chromatography (33% ethyl acetate in hexanes) provided {6-fluoro-3-methyl-4-[1-(pyrrolidine-1-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (86.5 mg, 81%). MS cald. for C23H30FN2O4S [(M+H)+]: 449, obsd. 449.2.

Provenance & Evidence