Diisopropylethylamine → HCID 178490378, compound

Participants

Reaction Steps

To 150 mg (0.45 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxy-phenyl)propanoic acid dissolved in 3 ml of dichloromethane and 0.5 ml of dimethylformamide are added 0.16 ml (0.90 mmol) of diisopropylethylamine, 161 mg (0.50 mmol) of TBTU and 133 mg (0.50 mmol) of 4-tert-butylcarbamoyl-4-cyclohexylpiperidine. After 3 hours, the solution is washed with 1N sodium hydroxide solution and the organic products are extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and concentrated. The crude product obtained is purified by preparative TLC (eluent: dichloromethane/methanol 85/15). 29 mg of 4-tert-butylcarbamoyl 4-cyclohexyl-1-[2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)propionyl]-piperidine in the form of a white powder are obtained in a yield of 11%.

Provenance & Evidence