1H-1,2,4-Triazole → 5-methyl-7-(1-methyl-1H-indol-2-yl)-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2374985Notes

Reaction equation

HRID 2374985 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:13][CH:14]([C:16]1[N:21]=[N:20][C:19]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[N:18][CH:17]=1)[CH3:15])=O.N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:15][C:14]1[N:13]=[C:11]([C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:21]2[C:16]=1[CH:17]=[N:18][C:19]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[N:20]2

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 587119791-methyl-N-[1-(3-{[4-(methyloxy)phenyl]amino)-1,2,4-triazin-6-yl)ethyl]-1H-indole-2-carboxamide2×

Product 1

HCID 113265905-methyl-7-(1-methyl-1H-indol-2-yl)-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amineYield 7.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Applying the Cyclization Procedure 2, using 1-methyl-N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]-1H-indole-2-carboxamide (Intermediate 56) (151 mg, 0.38 mmol), pyridine (3.7 mL), 1,2,4 triazole (78 mg, 1.13 mmol) and phosphorus oxychloride (0.052+0.052 mL, 1.12 mmol), to afford 5-methyl-7-(1-methyl-1H-indol-2-yl)-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (11 mg) as a yellow solid. MS m/z 385 (M+1).

Sources & evidence

ORD record
ord-7ec402ad69284989a2223c5dc1b2cc35
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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