Potassium Phosphate, Tribasic → N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-1-(1-methyl-1H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide

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Reaction Steps

To a stirred mixture of N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide (91 mg, 0.3 mmol) (prepared as described in Example 28) and 2-bromo-1-methyl-1H-imidazole (48.3 mg, 0.3 mmol) in 1,4-dioxane (6 ml) was added potassium phosphate (318 mg, 1.5 mmol), copper (I) iodide (57.1 mg, 0.3 mmol) and trans-N,N-dimethylcyclohexane-1,2-diamine (0.047 ml, 0.3 mmol) and the mixture was heated at reflux under argon for 3 hours. The mixture was cooled to room temperature and partitioned between saturated sodium hydrogen carbonate solution and dichloromethane. The organic extracts were separated, washed with water and brine, dried and evaporated. The residue was purified by mass-directed automated HPLC to give N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-1-(1-methyl-1H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide (22 mg, 19%). LC/MS [M+H]+=384, retention time=1.69 minutes.

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