Dimethylformamide → HCID 86674324, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of tert-butyl {3-nitro-5-[2-(3-oxo-1,4-diazepan-1-yl)-1,3-thiazol-5-yl]phenyl}[4-(trifluoromethyl)pyrimidin-2-yl]carbamate (314 mg, 0.542 mmol) in ethanol (9 mL) at room temperature under nitrogen, was added iron (605 mg, 10.84 mmol) and a saturated aqueous solution of ammonium chloride (0.25 mL). The mixture was stirred at 40° C. for 30 minutes. N,N′-dimethylformamide (5 mL) was added and the mixture was stirred at 40° C. for 3 hours. An additional portion of iron (300 mg, 5.4 mmol) and saturated aqueous solution of ammonium chloride (1.1 mL) were then added and the resulting mixture was stirred at 40° C. for 2 hours. The reaction was then cooled to room temperature, and concentrated under reduced pressure to remove volatiles. The resulting suspension was filtered through celite, rinsing successively with N,N′-dimethylformamide, ethyl acetate, dichloromethane, and 2-methyltetrahydrofuran. The filtrate was concentrated to remove the volatiles, then diluted with ethyl acetate, washed with water (5×), brine (1×), dried over sodium sulfate, and concentrated to provide a beige solid. This solid was swished in 1:1 ethyl acetate/hexane, the solids collected by filtration, rinsed successively with 1:1 ethyl acetate/hexane and hexane, and dried to afford 250 mg (0.46 mmol, 85%) of tert-butyl {3-amino-5-[2-(3-oxo-1,4-diazepan-1-yl)-1,3-thiazol-5-yl]phenyl}[4-(trifluoromethyl)pyrimidin-2-yl]carbamate as a beige solid.

Provenance & Evidence