Methanesulfonyl chloride → HCID 71539429, compound

Participants

Reaction Steps

To a stirred solution of 2-(4-(aminomethyl)-3-chlorophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (90 mg, 0.195 mmol) in pyridine, cooled to 0° C., were added methanesulfonyl chloride (90 mg). The resulting reaction mixture was stirred for 15 h at room temperature. The mixture dissolved in dichloromethane and washed with 1N HCl. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography. 2-(3-Chloro-4-(methylsulfonamidomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (example 77) (87 mg) was obtained as 83% yield. 1H NMR (300 MHz, CDCl3) 7.77 (d, 1H, J=8.04 Hz, Ar), 7.58 (d, 1H J=8.07 Hz, Ar), 7.39 (d, 1H, J=7.86 Hz, Ar), 7.28 (m, 4H, Ar), 7.13 (m, 2H, Ar), 5.59 (t, 1H, NH), 4.82 (t, 1H, NH), 4.47 (d, 2H, J=6.03 Hz, CH2), 4.37 (d, 2H, J=6.39, CH2), 3.44 (q, 1H, CH), 2.88 (s, 3H, mesyl), 2.38 (s, 3H, methyl), 1.44 (d, 3H, J=7.14 Hz, CH3)

Provenance & Evidence