Hydrochloric Acid → HCID 67103613, compound

Participants

Reaction Steps

A mixture of N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide (100 mg, 0.33 mmol) (prepared as described in Example 28) and potassium carbonate (91 mg, 0.66 mmol) in DMF (1 ml) was stirred at room temperature for 10 minutes and 4-(2-chloroethyl)morpholine hydrochloride (61 mg, 0.33 mmol) was added. The mixture was stirred for 30 minutes and then heated at 60° C. for 3 h and 80° C. for 2 h. The mixture was cooled to room temperature and sodium hydride (40 mg, 60% dispersion in oil, 1 mmol) was added and the mixture heated at 50° C. for 16 h. The reaction mixture was cooled to room temperature and diluted with dichloromethane. The solution was washed with saturated sodium hydrogen carbonate solution and brine, dried and evaporated. The residue was purified by mass-directed automated HPLC to give two components with same molecular ion. Each component was converted to the corresponding HCl salt by dissolving the product from mass-directed automated HPLC in methanol/dichloromethane, adding an excess of 1M HCl in ether, evaporating the solvent, co-evaporating the residue with methanol and ether. The residue was triturated with ether/heptane and the solid collected and dried to give N-[(2-Chloro-3,4-difluorophenyl)methyl]-3-methyl-1-[2-(4-morpholinyl)ethyl]-2-oxo-4-imidazolidinecarboxamide hydrochloride (22 mg, 15%) (LC/MS [M+H]+=417, retention time=1.40 minutes) and N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-1-[2-(4-morpholinyl)ethyl]-2-oxo-4-imidazolidinecarboxamide hydrochloride (6 mg, 4%) (LC/MS [M+H]+=417, retention time=1.55 minutes).

Provenance & Evidence