1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (3R)-N-(4-chlorophenyl)-3-cyclohexyl-4-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-4-oxobutanamide

Participants

Reaction Steps

To a solution of (2R)-4-((4-chlorophenyl)amino)-2-cyclohexyl-4-oxobutanoic acid (0.27 g) obtained in Example 5b) and HOBt (0.20 g) in acetonitrile (10 ml) was added WSC (0.25 g), and the reaction mixture was mixed at room temperature for 15 minutes. Then, 5-methyl-2-(4-piperidinyl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride (0.26 g), DBU (0.27 g) and triethylamine (0.27 g) were added thereto. The reaction mixture was mixed at room temperature for 15 hours, the solvent was then distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with an aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, the residue was purified with silica gel column (ethyl acetate to ethyl acetate/methanol=10/1), and the product was washed with ethyl acetate-hexane to obtain the title compound as colorless powder (0.13 g, 29%).

Provenance & Evidence