Trichloroacetyl isocyanate → HCID 59026695, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, a solution of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-5-oxido-1H-imidazo[4,5-c][1,5]naphthyridine (1.64 g, 3.90 mmol) in anhydrous dichloromethane (50 mL) was cooled to 6° C., and a solution of trichloroacetyl isocyanate (0.51 mL, 4.29 mmol) in dichloromethane (5 mL) was added dropwise. The solution was stirred for 30 minutes, and then the solvent was removed under reduced pressure. The residue was treated with sodium methoxide in methanol (10 mL of a 25% w/w solution) and methanol (40 mL). The resulting mixture was stirred for 18 hours at room temperature. A precipitate was present and was isolated by filtration, washed with methanol and diethyl ether, and dried under high vacuum at 80° C. for 18 hours to provide 0.999 g of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine as a white solid, mp 190.0-191.0° C.

Provenance & Evidence