Triethylamine → 2-(2,6-Dichlorophenyl)-3H-benzimidazole-5-carboxylic acid [2-(4-chlorophenyl)-1-methyl-2-oxoethyl]-amide

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Reaction Steps

A mixture of 1-(4-chlorophenyl)-2-aminopropiophenone hydrochloride (365 mg, 1.66 mmol), 2-(2,6-dichlorophenyl)-3H-benzimidazole-5-carbonyl chloride hydrochloride (600 mg, 1.66 mmol) (Example 1-27, step E), and triethylamine (924 μL, 671 mg, 6.63 mmol) in THF (25 mL) was stirred at RT for 18 hrs. The solution was poured into ethyl acetate and extracted with water and brine. The organic layer was dried, filtered, and the solvent removed under reduced pressure. The residue was chromatographed using a gradient of 50-90% heptane/ethyl acetate to give the title compound). MS: m/z 473.9 (M+1); H1-NMR (acetone-d6): δ 8.57 (m, broad, 1H), 8.37 (m, 3H), 8.11 (m, broad, 1H), 7.83 (m, 5H), 5.92 (quintet, J=7.2 Hz, 1H), 1.75 (d, J=7.0 Hz, 3H).

Provenance & Evidence