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

HRID 2374889Notes

Reaction equation

HRID 2374889 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH:10]([C:12]2[N:17]=[N:16][C:15]([NH:18][C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)=[N:14][CH:13]=2)[CH3:11])=O)=[CH:4][CH:3]=1.N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[Br:1][C:2]1[S:6][C:5]([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:4][CH:3]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 58711971HCID 58711971, compound2×

Product 1

HCID 112368897-(5-bromothien-2-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amineYield 7.8%

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)thiophene-2-carboxamide (Intermediate 22) (0.35 g, 0.70 mmol) and 1,2,4-triazole (290 mg, 4.2 mmol) in pyridine (5 mL) and phosphorus oxychloride (0.200 mL, 2.1 mmol) gave 7-(5-bromothien-2-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (0.026 g) as a yellow solid. 1H NMR (DMSO-d6): δ9.70 (s, 1H), 9.24 (s, 1H), 7.83 (d, J=4.0 Hz, 1H), 7.38 (d, J=4.0 Hz, 1H), 7.10 (s, 2H), 3.81 (s, 6H), 3.66 (s, 3H), 2.51 (s, 3H). MS m/z 476, 478 (M+1, M+3).

Sources & evidence

ORD record
ord-378b4c6920a046b0acac5ae41ddb8acd
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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