4-Methylmorpholine → N-(3-(4-(2,3-dichlorophenyl)piperazin-1-yl)-2-hydroxypropyl)-2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxamide

Participants

Reaction Steps

To a mixture of lithium 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylate (compound 13a, 150 mg, 0.67 mmol), 1-amino-3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propan-2-ol dihydrochloride (compound 41, 300 mg, 0.80 mmol), EDCI (260 mg, 1.34 mmol) and HOBt (180 mg, 1.34 mmol) in anhydrous DMF (7 mL) was added NMM (370 μl, 3.35 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 (134 mg, 40%) as a white solid.

Provenance & Evidence