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

HRID 2374983Notes

Reaction equation

HRID 2374983 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:11]=[N:12][C:13]([CH:16]([NH:18][C:19](=O)[CH:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:21])[CH3:17])=[CH:14][N:15]=2)=[CH:5][CH:4]=1.N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:17][C:16]1[N:18]=[C:19]([CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])[N:12]2[C:13]=1[CH:14]=[N:15][C:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[N:11]2

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 58711994N-[1-(3-{[4-(methyloxy)phenyl]amino)-1,2,4-triazin-6-yl)ethyl]-2-phenylpropanamide2×

Product 1

HCID 113258305-methyl-N-[4-(methyloxy)phenyl]-7-(1-phenylethyl)imidazo[5,1-f][1,2,4]triazin-2-amineYield 12.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Applying the Cyclization Procedure 2, using N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]-2-phenylpropanamide (Intermediate 55) (129 mg, 0.34 mmol), pyridine (3.4 mL), 1,2,4 triazole (71 mg, 1.03 mmol) and phosphorus oxychloride (0.048+0.048 mL, 1.03 mmol), to afford 5-methyl-N-[4-(methyloxy)phenyl]-7-(1-phenylethyl)imidazo[5,1-f][1,2,4]triazin-2-amine (15 mg) as a yellow solid. MS m/z 360 (M+1).

Sources & evidence

ORD record
ord-a40d9fff062d4f738e532110d3b54fe0
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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