Reaction Steps
Using general procedure E, 4-[(3-cyano-benzyl)-(1-{3-[(4,6-dimethyl-pyrimidine-5-carbonyl)-amino]-1-methyl-propyl}-piperidin-4-yl)-amino]-benzoic acid (see EXAMPLE 129) (50 mg, 0.09 mmol) and morpholine (29 μL, 0.33 mmol) afforded COMPOUND 167 as a white solid (48 mg, 87%). 1H NMR (CDCl3) δ 0.84-1.18 (m, 2H), 1.03 (d, 3H, J=6.6 Hz), 1.50-1.60 (m, 1H), 1.70-1.84 (m, 3H), 2.14-2.26 (m, 1H), 2.51 (s, 6H), 2.53-2.65 (m, 1H), 2.71-2.92 (m, 3H), 3.27-3.39 (m, 1H), 3.57-3.92 (m, 10H), 3.96 (s, 2H), 6.52 (d, 2H, J=8.4 Hz), 7.25-7.30 (m, 2H), 7.43-7.59 (m, 4H), 8.54 (br s, 1H), 8.90 (s, 1H). 13C NMR (CDCl3) δ 13.84, 22.36, 29.54, 30.83, 31.12, 40.49, 43.87, 48.45, 52.39, 56.04, 60.76, 67.36, 77.61, 112.53, 113.14, 123.98, 129.89, 130.08, 131.17, 141.51, 149.88, 157.99, 163.53, 166.57, 171.00. ES-MS m/z 610 (M+H). Anal. Calcd. for C35H43N7O3.0.2CH2Cl2.0.1H2O: C, 67.26; H, 6.99; N, 15.60. Found. C, 67.44; H, 7.12; N, 15.30.
