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 133) (54 mg, 0.10 mmol) and piperazine (26 mg, 0.30 mmol) afforded COMPOUND 135 as a white solid (19 mg, 31%). 1H NMR (CDCl3) δ 0.83-1.13 (m, 2H), 1.03 (d, 3H, J=6.3 Hz), 1.49-1.79 (m, 5H), 2.20 (t, 1H, J=11.7 Hz), 2.51 (s, 6H), 2.60 (t, 1H, J=10.8 Hz), 2.76-2.86 (m, 7H), 3.29-3.37 (m, 1H), 3.58-3.72 (m, 4H), 3.82-3.88 (m, 1H), 3.96 (s, 2H), 6.52 (d, 2H, J=8.7 Hz), 7.25-7.26 (m, 2H), 7.44-7.56 (m, 4H), 8.54 (br s, 1H), 8.90 (s, 1H). 13C NMR (CDCl3) δ 13.46, 21.97, 29.16, 30.38, 30.82, 39.97, 41.22, 42.71, 43.57, 46.25, 48.11, 51.94, 55.66, 60.20, 112.14, 112.70, 118.91, 124.15, 129.38, 129.45, 129.70, 130.77, 130.90, 141.23, 149.34, 157.56, 163.12, 166.27, 170.60. ES-MS m/z 609 (M+H). Anal. Calcd. for C35H44N8O2.0.5CH2Cl2.0.1H2O: C, 65.29; H, 6.98; N, 17.16. Found. C, 65.22; H, 7.12; N, 16.78.
