1,2,3,4-Tetrahydro-4,4-dimethylisoquinoline → N,N-Dibutyl-4-chloro-1-(2-(4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(naphthalen-2-ylsulfonylcarbamoyl)phenyl)-5-methyl-1H-pyrazole-3-carboxamide

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Following a procedure analogous to that for the synthesis of Intermediate 93B, 2-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoic acid (Intermediate 91F, 32 mg, 0.051 mmol) and 4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline (Milestone Pharmtech, 9 mg, 0.056 mmol) were converted to the title compound (14 mg, 34%) following purification by preparative HPLC. 1H NMR (DMSO-d6, 1:1 mixture of amide rotamers) δ 8.64 (s, 1H), 8.20 (d, J=7.7 Hz, 1H), 8.14-7.90 (m, 5H), 7.78-7.59 (m, 3H), 7.36 (t, J=7.7 Hz, 1H), 7.26-7.13 (m, 2H), 7.11-7.02 (m, 0.5H), 6.99-6.89 (m, 0.5H), 4.85-4.20 (m, 2H), 3.58 (br s, 0.5H), 3.51-2.98 (m, 5H), 2.57-2.52 (m, 0.5H), 2.24 (s, 1.5H), 2.18 (s, 1.5H), 1.43-0.94 (m, 14H), 0.82 (t, J=7.3 Hz, 1H), 0.74 (t, J=7.3 Hz, 2H), 0.69 (t, J=7.4 Hz, 1.5H), 0.64 (t, J=7.4 Hz, 1.5H); MS(ESI+) m/z 768.3 (M+H)+.

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