4-Chloro-N-methylbenzenamine → 2-{2-[(4-Chlorophenyl)methyl carbamoyl]quinolin-6-yl}-1-cyclohexyl-1H-benzimidazole-5-carboxylic Acid Ethyl Ester

Participants

Reaction Steps

A solution of 100 mg (0.23 mmol) Compound 402a in 1 mL SOCl2 was allowed to stand at room temperature for 10 min and SOCl2 was removed. The residue was dissolved in 5 mL anhydrous CH2Cl2; 89 mg (0.69 mmol) DIEA, 84 mg (0.69 mmol) DMAP, 98 mg (0.69 mmol) 4-chloro-N-methylaniline were added; and the solution was vortexed and allowed to stand at room temperature overnight. The solvent was removed and the residue was chromatographed on silica gel using hexane/EtOAc as the eluent to yield 63 mg of yellow oil. MS: 576.24 (M+H+).

Provenance & Evidence