Reaction Steps
Using general procedure E, 4-((3-chloro-benzyl)-{1-[3-(2,6-dimethyl-benzoylamino)-1-methyl-propyl]-piperidin-4-yl}-amino)-benzoic acid (see EXAMPLE 86) (40 mg, 0.074) and aniline (8 μL, 0.08 mmol) afforded COMPOUND 89 as a white solid (32 mg, 71%). 1H NMR (CDCl3) δ 0.93-1.25 (m, 2H), 1.01 (d, 3H, J=6.3 Hz), 1.51-1.55 (m, 1H), 1.72-1.76 (m, 3H), 2.19 (t, 1H, J=11.1 Hz), 2.31 (s, 6H), 2.58 (t, 1H, J=11.1 Hz), 2.76-2.92 (m, 3H), 3.25-3.32 (m, 1H), 3.67-3.75 (m, 1H), 3.87 (s, 2H), 3.87-3.93 (m, 1H), 6.57 (d, 2H, J=8.7 Hz), 6.95-7.12 (m, 6H), 7.23-7.32 (m, 4H), 7.60 (d, 2H, J=7.8 Hz), 7.68 (d, 2H, J=8.4 Hz), 7.76 (s, 1H), 8.35 (br s, 1H). 13C NMR (CDCl3) δ 13.85, 19.55, 29.42, 30.70, 31.35, 40.22, 43.96, 48.59, 52.47, 56.25, 60.92, 112.50, 120.35, 122.88, 124.35, 124.61, 126.60, 127.47, 127.78, 128.89, 129.13, 129.37, 130.27, 134.44, 134.95, 138.80, 138.97, 142.01, 151.51, 165.65, 170.31. ES-MS m/z 623 (M+H). Anal. Calcd. for C38H43N4ClO2.0.2CH2Cl2: C, 71.65; H, 6.83; N, 8.75. Found. C, 71.64; H, 6.81; N, 8.84.
