N,N'-Dimethylethylenediamine → 4-Fluoro-N-{[2-oxo-6-(1H-1,2,4-triazol-1-yl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}benzamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-{[6-iodo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}-4-fluorobenzamide (50 mg, 0.081 mmol), 1,2,4-triazole (16.9 mg, 0.244 mmol), potassium phosphate (25.9 mg, 0.122 mmol), N,N′-dimethylethylenediamine (6.9 μL, 0.065 mmol) and copper iodide (I) (3.1 mg, 0.016 mmol) in DMF (0.4 mL) was stirred for 1 hour under heating at 110° C. The temperature of the solution was brought to room temperature, and the solution was diluted with ethyl acetate, which was washed sequentially with a saturated aqueous ammonium chloride solution and saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The residue was subjected to the same condition as in Example 154 to effect deprotection of the 4-methoxybenzyl group, whereby the objective compound (8.0 mg, 23%) was obtained as a pale white solid.

Provenance & Evidence