1H-1,2,4-Triazole → Methyl 3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzoate

Participants

Reaction Steps

In a similar manner as described for Example 9, methyl 3-{[(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)amino]carbonyl}benzoate (Intermediate 21) (0.26 g, 0.56 mmol) and 1,2,4-triazole (240 mg, 3.4 mmol) in pyridine (4 mL) and phosphorus oxychloride (0.16 mL, 1.7 mmol) gave methyl 3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzoate (0.16 g) as a yellow solid. 1H NMR (DMSO-d6): δ9.66 (s, 1H), 9.28 (s, 1H), 8.94 (dd, J=1.7, 1.3 Hz, 1H), 8.74 (ddd, J=8.5, 1.9, 1.2 Hz, 1H), 8.01 (ddd, J=7.7, 1.8, 1.2 Hz, 1H), 7.65 (dd, J=8.3, 7.9 Hz, 1H), 7.08 (s, 2H), 3.84 (s, 3H), 3.68 (s, 6H), 3.65 (s, 3H), 2.55 (s, 3H). MS m/z 450 (M+1).

Provenance & Evidence