1H-1,2,4-Triazole → 7-(5-bromopyridin-3-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2374885Notes

Reaction equation

HRID 2374885 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:31]=1)[C:7]([NH:9][CH:10]([C:12]1[N:17]=[N:16][C:15]([NH:18][C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=2)=[N:14][CH:13]=1)[CH3:11])=O.N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[Br:1][C:2]1[CH:31]=[C:6]([C:7]2[N:17]3[C:12]([CH:13]=[N:14][C:15]([NH:18][C:19]4[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=4)=[N:16]3)=[C:10]([CH3:11])[N:9]=2)[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 58711987HCID 58711987, compound2×

Product 1

HCID 113748287-(5-bromopyridin-3-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amineYield 7.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, 5-bromo-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)nicotinamide (Intermediate 20) (0.15 g, 0.31 mmol) and 1,2,4-triazole (128 mg, 1.9 mmol) in pyridine (4 mL) and phosphorus oxychloride (0.087 mL, 0.93 mmol) gave 7-(5-bromopyridin-3-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (0.011 g) as a yellow solid. 1H NMR (Acetone-d6): δ9.81-9.78 (m, 1H), 9.18 (s, 1H), 8.93-8.90 (m, 1H), 8.73-8.70 (m, 1H), 8.57 (s, 1H) 7.12 (s, 2H), 3.73 (s, 3H), 3.73 (s, 3H), 3.70 (s, 3H), 2.59 (s, 3H). MS m/z 471, 473 (M+1, M+3).

Sources & evidence

ORD record
ord-7dcca8c7cb6e40e4927ee8639c373e3d
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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