1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(4-(2-tert-butylphenyl)piperazin-1-yl)-N-(methylsulfonyl)-4-oxobutanamide

Participants

Reaction Steps

To a stirred solution of 4-(4-(2-tert-butylphenyl)piperazin-1-yl)-4-oxobutanoic acid obtained in Example 53 (0.100 g, 0.31 mmol), EDCI (0.090 g, 0.47 mmol), HOBt (0.064 g, 0.47 mmol) and diisopropylethylamine (0.163 g, 1.26 mmol) in methylene chloride (2.0 mL) was added methane-sulfonamide (0.031 g, 0.31 mmol) at room temperature. After 18 h the reaction mixture was diluted with ethyl acetate, washed with 1.0 M hydrochloric acid (5.0 mL), water (5.0 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 95:5 methylene chloride/MeOH) to provide 4-(4-(2-tert-butylphenyl)piperazin-1-yl)-N-(methylsulfonyl)-4-oxobutanamide (0.051 g, 41%) as an off-white solid, mp: 89-90° C.

Provenance & Evidence