Reaction Steps
Following a procedure analogous to that for the synthesis of Example 1,4-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acid (Intermediate 1F, 40 mg, 0.073 mmol) and 7-(2-(tert-butyldimethylsilyloxy)ethoxy)naphthalene-2-sulfonamide (Intermediate 50B, 33 mg, 0.087 mmol) were converted to the title compound (31 mg, 47%) after purification using flash column chromatography (gradient from 0% to 3% MeOH/CH2Cl2). 1H NMR (CDCl3, 2:1 mixture of amide rotamers) δ 8.62 (s, 1H), 8.11-8.09 (m, 1H), 7.97-7.96 (m, 1H), 7.89-7.88 (m, 2H), 7.84 (d, J=8.9 Hz, 1H), 7.55-7.52 (m, 1H), 7.40-7.38 (m, 2H), 7.23-7.07 (m, 3.5H), 6.85 (d, J=7.4 Hz, 0.5H), 4.75 (br s, 1H), 4.63 (br s, 1H), 4.42 (s, 1H), 4.27-4.24 (m, 2H), 3.85-3.81 (m, 2H), 3.46 (br s, 2H), 3.18-3.15 (m, 2H), 3.02 (br s, 1.5H), 2.84 (br s, 1.5H), 2.29 (s, 2H), 2.24 (s, 1H), 1.50-1.45 (m, 1H), 1.41-1.36 (m, 1H), 1.32-1.20 (m, 6H), 1.12-0.99 (m, 1H), 0.93-0.86 (m, 12H), 0.74 (t, J=7.4 Hz, 2H), 0.68 (t, J=7.2 Hz, 1H), 0.10 (s, 6H); MS(ESI+) m/z 914.3 (M+H)+.
