Benzyl 4-fluoro-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate → Benzyl 4-(3-(butyl(3,4-dichlorobenzyl)carbamoyl)-4-chloro-5-methyl-1H-pyrazol-1-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

Participants

Reaction Steps

Following a procedure analogous to that for the synthesis of Intermediate 1E, N-butyl-4-chloro-N-(3,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxamide (1.73 g, 4.62 mmol) and benzyl 4-fluoro-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (Intermediate 122B, 1.80 g, 4.62 mmol) were converted to the title compound (2.20 g, 64%). 1H NMR (CDCl3, mixture of amide rotamers) δ 8.24 (d, J=8.4 Hz, 1H), 8.16-8.09 (m, 1H), 7.53-7.03 (m, 12H), 6.98-6.76 (m, 1H), 5.41 (br s, 2H), 4.86-4.20 (m, 4H), 3.64-3.03 (m, 4H), 2.78 (br s, 2H), 2.37-2.17 (m, 3H), 1.61-1.38 (m, 1H), 1.36-1.21 (m, 2H), 1.18-1.01 (m, 1H), 0.97-0.83 (m, 2H), 0.80-0.67 (m, 1H); MS(ESI+) m/z 745.2 (M+H)+.

Provenance & Evidence