1H-1,2,4-Triazole → HCID 11363540, compound

HRID 2374883Notes

Reaction equation

HRID 2374883 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=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:6]=[CH:5][S:4][C:3]=1[C:7]1[N:17]2[C:12]([CH:13]=[N:14][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:16]2)=[C:10]([CH3:11])[N:9]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 587119593-bromo-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)thiophene-2-carboxamide2×

Product 1

HCID 11363540HCID 11363540, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, 3-bromo-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)thiophene-2-carboxamide (Intermediate 19) (0.23 g, 0.47 mmol) and 1,2,4-triazole (100 mg, 1.5 mmol) in pyridine (4 mL) and phosphorus oxychloride (0.070 mL, 0.75 mmol) gave 7-(3-bromothien-2-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (0.033 g) as a yellow solid. 1H NMR (CDCl3): δ8.82 (s, 1H), 7.47 (d, J=5.3 Hz, 1H), 7.13 (s, 1H), 7.10 (d, J=5.3 Hz, 1H), 6.89 (s, 2H), 3.80 (s, 3H), 3.75 (s, 6H), 2.63 (s, 3H). MS m/z 476, 478 (M+1, M+3).

Sources & evidence

ORD record
ord-e601fee3e1aa490299ab79c3efe669f7
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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