Reaction Steps
Using general procedure E, 4-[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(3-cyano-benzyl)-amino]-N-methyl-benzenesulfonamide (see EXAMPLE 151) (63 mg, 0.14 mmol) and 4,6-dimethyl-pyrimidine-5-carboxylic acid (23 mg, 0.15 mmol) gave COMPOUND 152 as a white solid (72 mg, 89%). 1H NMR (CDCl3) δ 1.00-1.17 (m, 2H), 1.02 (d, 3H, J=5.4 Hz), 1.55 (m, 1H), 1.74-1.78 (m, 3H), 2.21 (t, 1H, J=10.5 Hz), 2.50 (s, 6H), 2.58-2.62 (m, 4H), 2.75-2.85 (m, 3H), 3.34 (m, 1H), 3.77 (m, 2H), 4.05 (s, 2H), 4.44 (d, 1H, J=4.2 Hz), 6.56 (d, 2H, J=8.1 Hz), 7.47-7.72 (m, 5H), 8.35 (br s, 1H), 8.90 (s, 1H). 13C NMR (CDCl3) δ 13.52, 21.97, 28.92, 29.32, 30.31, 31.00, 39.75, 43.60, 48.08, 51.64, 55.73, 59.82, 112.00, 112.78, 118.79, 125.81, 129.25, 129.48, 129.64, 130.70, 130.88, 130.95, 140.36, 151.29, 157.53, 163.15, 166.30. ES-MS m/z 590 (M+H). Anal. Calcd. for C31H39N7O3S.0.6CH2Cl2: C, 59.24; H, 6.32; N, 15.30; S, 5.00. Found. C, 59.35; H, 6.37; N, 15.18; S, 4.87.
