Reaction Steps
To a 0.166 M solution of crude 3-{3-[2-(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazol-1-ylmethyl}-benzoyl chloride in methylene chloride (prepared in Example 63, 1.71 mL, 0.28 mmol) was added a 40% solution of dimethylamine in water (250 μL, 0.22 mmol) and the reaction stirred at 25° C. for 30 min. The solution was diluted with methylene chloride (40 mL), washed with water (2×20 mL), saturated aqueous brine solution (2×20 mL), dried over magnesium sulfate and concentrated in vacuo to an off white foam. Purification by flash column chromatography (Merck silica gel 60, 40-63 μm; 0% ethyl acetate/methylene chloride to 100% ethyl acetate/methylene chloride) afforded 3-{3-[2-(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazol-1-ylmethyl}-N,N-dimethyl-benzamide (72 mg, 46%) as a white powder: ESI-LRMS m/e calcd for C28H33ClN4O4S [M+] 556.19, found 557.27 [M+H+]; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02-1.19 (m, 2H, CH2), 1.36-1.78 (m, 8H, 4×CH2), 2.02-2.17 (m, 1H, CH), 2.84 (s, 3H, NCH3), 2.94 (s, 3H, NCH3), 3.32 (s, 3H, SO2CH3), 3.82-3.91 (m, 1H, CH), 5.21 (s, 2H, NCH2), 6.45 (d, J=2.3 Hz, 1H, Ar), 7.17-7.32 (m, 3H, Ar), 7.33-7.40 (m, 1H, Ar), 7.55 (dd, Jo=8.3, Jm=1.7 Hz, 1H, Ar), 7.65 (d, Jm=1.7 Hz, 1H, Ar), 7.73 (d, J=2.3 Hz, 1H, Ar), 7.97 (d, Jo=8.3 Hz, 1H, Ar), 10.77 (s, 1H, NH).
