Thionyl Chloride → HCID 11466081, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-benzoyl-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (Intermediate 28) (95 mg, 0.18 mmol) in 1,2-dichloroethane was added catalytic dimethylformamide (3 drops) and thionyl chloride (0.36 mL, 5.0 mmol). The mixture was heated at 50° C. for 14 hours. After cooling to room temperature the mixture was concentrated under vacuum. The resulting solid was taken up in a mixture of dichloromethane and methanol, then concentrated ammonium hydroxide was added until the solution was basic. The solution was then concentrated under vacuum and purified by reverse-phase HPLC to give (3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)-amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)(phenyl)-methanone (8 mg) as a yellow solid. 1H NMR (DMSO-d6): δ9.63 (s, 1H), 9.26 (s, 1H), 8.80 (d, J=7.87 Hz, 1H), 8.61 (s, 1H), 7.74-7.80 (m, 3H), 7.63 (t, J=7.69 Hz, 2H), 7.68 (t, J=7.69 Hz, 2H), 7.05 (s, 2H), 3.68 (s, 6H), 3.62 (s, 3H), 2.52 (s, 3H). MS m/z 495 (M+1).

Provenance & Evidence