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

HRID 2374887Notes

Reaction equation

HRID 2374887 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[N:15]=[N:16][C:17]([CH:20]([NH:22][C:23]([C:25]3[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=3)[C:28]([O:30][CH3:31])=[O:29])=O)[CH3:21])=[CH:18][N:19]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:21][C:20]1[N:22]=[C:23]([C:25]2[CH:26]=[C:27]([CH:32]=[CH:33][CH:34]=2)[C:28]([O:30][CH3:31])=[O:29])[N:16]2[C:17]=1[CH:18]=[N:19][C:14]([NH:13][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=1)=[N:15]2

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 58711966Methyl 3-{[(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)amino]carbonyl}benzoate2×

Product 1

HCID 11775266Methyl 3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}benzoateYield 63.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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).

Sources & evidence

ORD record
ord-44abbe92971a4af4a66ecb103f0635e1
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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