Phosphorus oxychloride → HCID 11465304, compound

Participants

Reaction Steps

To a solution of 4-(trifluoromethyl)-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (Intermediate 27) (241 mg, 0.51 mmol) in 1,2-dichloroethane (20 mL) was added phosphorus oxychloride (0.37 mL, 4.0 mmol). The mixture was heated to reflux for 24 hours. After cooling to room temperature, the mixture was diluted with DCM and aqueous (saturated) Na2CO3. The aqueous was extracted with DCM and the combined organic layers were washed with brine, dried over Na2SO4, concentrated under vacuum and purified by silica gel chromatography to give 5-methyl-7-[4-(trifluoromethyl)phenyl]-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (0.007 g) as yellow solid. 1H NMR (CDCl3): δ8.85 (s, 1H), 8.86 (d J=8.24 Hz, 2H), 7.72 (d, J=8.24 Hz, 2H), 6.88 (m, 3H), 3.87 (s, 3H), 3.83 (s, 6H), 2.63 (s, 3H). MS m/z 459 (M+1).

Provenance & Evidence