Acetic Acid → 6-chloro-4-(4-chlorobenzoyl)-1-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-7-methyl-1,3,4,5-tetrahydro-benzo[e][1,4]-diazepin-2-on

Participants

Reaction Steps

140 mg (0.37 mmol) of ethyl [(2-amino-6-chlorobenzyl)-(4-chlorobenzoyl)amino]acetate and 89 mg (0.44 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzaldehyde were dissolved in 5 ml of dichloromethane. 0.042 ml (0.74 mmol) of acetic acid was added to the obtained solution, and they were stirred at room temperature for 30 minutes. 195 mg (0.93 mmol) of sodium triacetoxyborohydride was added to the obtained solution, and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in a mixture of 5 ml of 1 N sodium hydroxide and 5 ml of ethanol, and they were stirred at room temperature for 4 hours. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 5 ml of dichloromethane. 74 mg (0.44 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.1 ml (0.74 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. The solvent was evaporated and the obtained crude product was dissolved in 5 ml of 4N solution of hydrogen chloride in dioxane. The obtained solution was stirred at room temperature for 3 hours. The solvent was evaporated and the obtained crude product was treated in the same manner as in Step 3 in Example 1 to obtain the title compound.

Provenance & Evidence