1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-(3-Methylphenyl)urea

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Reaction Steps

To a solution of N-[(3RS)-1-hydroxycarbonylmethyl-5-(2-fluorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea (0.295 g) and 8-methyl-3,8-diazabicyclo[3.2.1]octane dihydrochloride (0.189 g) in N,N-dimethylformamide (10 ml) was added l-ethyl-3-(3'-dimethylaminopropyl)carbodiimide hydrochloride (0.150 g), 1-hydroxy-1H-benzotriazole monohydrate (0.120 g) and a solution of triethylamine (0.255 g) in N,N-dimethylformamide (2 ml). The. mixture was stirred overnight at ambient temperature. Then the mixture was heated at 80° C. for 1 hour. The mixture was concentrated in vacuo. The residue was treated with water, alkalized with sodium carbonate and extracted with chloroform. The extract was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with an eluent of a mixture of chloroform and methanol (50:1) to give N-[(3RS)-5-(2-fluorophenyl)-I-(8-methyl-3,8-diazabicyclo[3.2.1]-oct-3-yl)]carbonylmethyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea (0.300 g) as a colorless crystal.

Provenance & Evidence