N-Butyl-4-iodoaniline → N-Butyl-4-chloro-N-(4-iodophenyl)-5-methyl-1-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1H-pyrazole-3-carboxamide

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis Intermediate 122G, 4-chloro-5-methyl-1-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1H-pyrazole-3-carboxylic acid (Intermediate 122F, 116 mg, 0.18 mmol) and N-butyl-4-iodoaniline (Okano, K. et al., Org. Lett., 5:4987-4990 (2003)) (59 mg, 0.22 mmol) were converted to the title compound (7 mg, 41%). 1H NMR (MeOD, 1:1 mixture of amide rotamers) δ 8.65 (s, 1H), 8.15-8.07 (m, 1.5H), 8.05-8.00 (m, 3.5H), 7.95 (d, J=8.0 Hz, 1H), 7.69-7.54 (m, 3H), 7.45-7.31 (m, 2H), 7.20-7.17 (m, 4H), 7.03-7.00 (m, 0.5H), 6.97-6.96 (m, 0.5H), 6.70 (d, J=8.6 Hz, 1H), 6.43 (br s, 1H), 4.93 (br s, 0.5H), 4.68 (br s, 0.5H), 4.48 (br s, 0.5H), 4.35 (br s, 0.5H), 3.83 (br s, 1H), 3.71 (br s, 1H), 3.61-3.45 (m, 2H), 3.11-3.01 (m, 1H), 2.92-2.78 (m, 1H), 2.16 (s, 3H), 1.41-1.22 (m, 4H), 0.91-0.80 (m, 3H); MS(ESI+) m/z 886.8 (M+H)+.

Provenance & Evidence