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

HRID 2374981Notes

Reaction equation

HRID 2374981 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([NH:13][CH:14]([C:16]2[N:21]=[N:20][C:19]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[N:18][CH:17]=2)[CH3:15])=O)=[CH:3]1.N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:15][C:14]1[N:13]=[C:11]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)[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 587119291-methyl-N-[1-(3-{[4-(methyloxy)phenyl]amino)-1,2,4-triazin-6-yl)ethyl]-1H-indole-3-carboxamide2×

Product 1

HCID 114859285-methyl-7-(1-methyl-1H-indol-3-yl)-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amineYield 54%

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-3-carboxamide (Intermediate 54) (107 mg, 0.26 mmol), pyridine (2.65 mL), 1,2,4 triazole (55 mg, 0.80 mmol) and phosphorus oxychloride (0.037+0.010 mL, 0.50 mmol), to afford 5-methyl-7-(1-methyl-1H-indol-3-yl)-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (54 mg) as a yellow solid. MS m/z 385 (M+1).

Sources & evidence

ORD record
ord-9bdd91c11d7445b297a8bc0069cb8e11
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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