Reaction Steps
Using general procedure E, 4-(benzyl-{1-[3-(2,6-dimethyl-4-pyridin-4-yl-benzoylamino)-1-methyl-propyl]-piperidin-4-yl}-amino)-benzoic acid (see EXAMPLE 91) (60 mg, 0.10 mmol) and ammonium chloride (22 mg, 0.41 mmol) afforded COMPOUND 92 as a white solid (43 mg, 71%). 1H NMR (CDCl3) δ 1.02 (d, 3H, J=5.7 Hz), 1.06-1.35 (m, 2H), 1.51-1.62 (m, 1H), 1.69-1.86 (m, 3H), 2.13-2.31 (m, 1H), 2.40 (s, 6H), 2.52-2.63 (m, 1H), 2.73-2.94 (m, 3H), 3.20-3.40 (m, 2H), 3.62-3.71 (m, 1H), 3.89 (s, 2H), 5.79 (br s, 2H), 6.49 (d, 2H, J=8.1 Hz), 6.84-6.93 (m, 2H), 7.12-7.22 (m, 3H), 7.25-7.33 (m, 2H), 7.41-7.48 (m, 2H), 7.57 (d, 2H, J=8.1 Hz), 8.20 (br s, 1H), 8.60-8.67 (m, 2H). 13C NMR (CDCl3) δ 13.45, 19.34, 29.05, 30.40, 31.30, 39.60, 43.73, 48.18, 51.98, 55.72, 60.12, 111.66, 120.60, 121.49, 125.76, 126.06, 126.75, 128.51, 129.11, 135.24, 138.06, 139.02, 139.21, 147.61, 150.35, 151.34, 169.08, 169.34. ES-MS m/z 590 (M+H).
