4-Methylmorpholine → 1-(4-chlorophenyl)-N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)-2-hydroxy propyl)-2-propyl-1H-imidazole-4-carboxamide

Participants

Reaction Steps

To a mixture of lithium 1-(4-chlorophenyl)-2-propyl-1H-imidazole-4-carboxylic acid (compound 6, 150 mg, 0.57 mmol), 1-amino-3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propan-2-ol dihydrochloride (compound 41, 260 mg, 0.68 mmol), EDCI (165 mg, 0.85 mmol) and HOBt (154 mg, 1.14 mmol) in anhydrous DMF (7 mL) was added NMM (190 μl, 1.71 mmol). The reaction mixture was stirred at room temperature for 15 hrs. The mixture was concentrated under reduced pressure. The residue was diluted with CH2Cl2, and washed with water. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product was purified by preparative HPLC (purification system, Gilson) to provide the title compound (74 mg, 24%) as a white solid.

Provenance & Evidence