4-bromo-N,N-dibutyl-5-methyl-1H-pyrazole-3-carboxamide → Ethyl 4-(4-bromo-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

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Following a procedure analogous to that for the synthesis of Intermediate 1E, 4-bromo-N,N-dibutyl-5-methyl-1H-pyrazole-3-carboxamide (646 mg, 2.04 mmol) and ethyl 4-fluoro-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (Intermediate 1D, 1.07 g, 3.27 mmol) were converted to the title compound (660 mg, 48%). 1H NMR (CDCl3, 2:1 mixture of amide rotamers) δ 8.24-8.19 (m, 1H), 8.14-8.10 (m, 1H), 7.45-7.39 (m, 1H), 7.25-7.09 (m, 3.5H), 6.88 (d, J=7.3 Hz, 0.5H), 4.78 (d, J=8.8 Hz, 1H), 4.49-4.36 (m, 3H), 3.71-2.69 (m, 8H), 2.32 (s, 2H), 2.28 (s, 1H), 1.54-1.27 (m, 8.5H), 1.11 (d, J=7.7 Hz, 2H), 0.92 (q, J=7.2 Hz, 3.5H), 0.79 (t, J=8.0 Hz, 3H); MS(ESI+) m/z 625.3 (M+H)+.

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