Benzenemethanamine, N-butyl-3,4-dichloro- → N-Butyl-4-chloro-N-(3,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxamide

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Reaction Steps

Following a procedure analogous to that for the synthesis of Intermediate 168A, 4-chloro-5-methyl-1H-pyrazole-3-carboxylic acid (1.50 g, 9.32 mmol) and N-(3,4-dichlorobenzyl)butan-1-amine (Intermediate 126, 2.16 g, 9.32 mmol) provided the title compound (1.67 g, 48%) as a colorless oil. 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 7.50-7.32 (m, 2H), 7.24-7.06 (m, 1H), 4.79-4.55 (m, 2H), 3.47-3.26 (m, 2H), 2.34-2.19 (m, 3H), 1.71-1.46 (m, 2H), 1.35 (br s, 1H), 1.18 (br s, 1H), 0.93 (d, J=6.4 Hz, 1.5H), 0.81 (d, J=6.8 Hz, 1.5H); MS(ESI+) m/z 376.0 (M+H)+.

Provenance & Evidence