7-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline → N,N-Dibutyl-4-chloro-5-methyl-1-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(7-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-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, 21 mg, 0.034 mmol) and 7-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline (7 mg, 0.037 mmol) were converted to the title compound (20 mg, 71%) following purification by preparative HPLC. 1H NMR (1:1 CD3OD:CDCl3, 1.5:1 mixture of amide rotamers) δ 8.69-8.58 (m, 1H), 8.19-8.13 (m, 1H), 8.08-8.02 (m, 2H), 8.01-7.97 (m, 1H), 7.95-7.91 (m, 1H), 7.90-7.86 (m, 1H), 7.60-7.54 (m, 2H), 7.45-7.34 (m, 2.5H), 7.28-7.23 (m, 1H), 7.17-7.14 (m, 0.5H), 4.89-4.64 (m, 1.5H), 4.52 (s, 1H), 4.16-4.02 (m, 0.5H), 3.70-3.34 (m, 2.5H), 3.24-2.75 (m, 4.5H), 2.28 (s, 2H), 2.23 (s, 1H), 1.51-0.93 (m, 8H), 0.87 (dt, J=17.8, 7.4 Hz, 3H), 0.75 (t, J=7.4 Hz, 2H), 0.64 (t, J=7.4 Hz, 1H); MS(ESI+) m/z 808.3 (M+H)+.

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