Diisopropylethylamine → HCID 86686909, 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 2,6-dichlorobenzenesulfonyl chloride (116 mg, 0.47 mmol). After stirring for ˜25 minutes at 0° C., the light yellow reaction mixture was allowed to warm to room temperature and then was stirred for 6.5 hours at room temperature under nitrogen. During this time, some solvent had evaporated. Methylene chloride (˜10 mL) and water (˜25 mL) were added and the mixture was extracted with methylene chloride (2×25 mL). The combined extracts were washed with brine solution, dried over anhydrous MgSO4, filtered, concentrated, and purified by silica gel chromatography (eluting with 25% ethyl acetate/hexanes) to give {4-[1-(2,6-dichloro-benzenesulfonyl)-piperidin-4-yl]-6-fluoro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (96 mg, 77%) as a light yellow product. MS cald. for C25H25Cl2FNO4S [(M+H)+]: 524, obsd. 524.1.

Provenance & Evidence