Ammonia → N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-(1-methyl-1H-pyrazol-5-yl)-2-oxo-4-imidazolidinecarboxamide

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Reaction Steps

To a stirred mixture of N-[(2,4-dichlorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide (200 mg, 0.662 mmol) (prepared as described in Example 30), 5-iodo-1-methyl-1H-pyrazole (165 mg, 0.794 mmol) in 1,4-dioxane (20 ml) was added potassium phosphate (703 mg, 3.31 mmol), copper (I) iodide (126 mg, 0.662 mmol) and trans-N,N-dimethylcyclohexane-1,2-diamine (0.104 ml, 0.662 mmol) and the reaction mixture was heated at reflux under argon for 18 hours. After cooling to room temperature, ethyl acetate (20 ml), water (10 ml) and 0.880 ammonia solution (5 ml) were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×20 ml). The organic extracts were combined, washed with citric acid solution (20 ml), water (10 ml) and brine (10 ml), dried and evaporated. The residue was purified by silica gel chromatography eluting with 0-10% methanol in dichloromethane followed by mass-directed automated HPLC to give N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-(1-methyl-1H-pyrazol-5-yl)-2-oxo-4-imidazolidinecarboxamide (40 mg, 16%). LC/MS [M+H]+=382, retention time=2.12 minutes.

Provenance & Evidence