4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-5-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acid → N,N-Dibutyl-5-(4-(8-chloronaphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1-methyl-1H-imidazole-4-carboxamide

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis of Example 265, 4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-5-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoic acid (150 mg, 0.29 mmol) and 8-chloronaphthalene-2-sulfonamide (Intermediate 5, 140 mg, 0.58 mmol) were converted to the title compound (26 mg, 12%). 1H NMR (CD3OD, 1:1 mixture of amide rotamers) δ 8.99 (s, 1H), 8.18-8.09 (m, 3H), 8.05 (dd, J=8.4, 2.0 Hz, 1H), 7.94-7.91 (m, 1H), 7.72 (dd, J=7.2, 1.2 Hz, 1H), 7.69 (s, 0.5H), 7.62-7.55 (m, 1.5H), 7.42 (dd, J=8.0, 4.8 Hz, 1H), 7.21-7.13 (m, 3.5H), 6.93 (d, J=8.0 Hz, 0.5H), 4.78 (br s, 0.5H), 4.62-4.49 (m, 1.5H), 3.90 (br s, 0.5H), 3.60 (br s, 0.5H), 3.50 (s, 3H), 3.49-3.39 (m, 2H), 3.24 (t, J=6.4 Hz, 0.5H), 3.18-3.13 (m, 1.5H), 2.90 (br s, 1.5H), 2.85-2.65 (m, 2.5H), 1.50-1.09 (m, 8H), 0.89-0.79 (m, 6H); MS(ESI+) m/z 742.2 (M+H)+.

Provenance & Evidence