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

HRID 2374975Notes

Reaction equation

HRID 2374975 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1[C:5]([NH:7][CH:8]([C:10]1[N:15]=[N:14][C:13]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[N:12][CH:11]=1)[CH3:9])=O.P(Cl)(Cl)(Cl)=O>ClCCCl>[CH3:9][C:8]1[N:7]=[C:5]([C:4]2[CH:25]=[CH:26][CH:27]=[CH:28][C:3]=2[O:2][CH3:1])[N:15]2[C:10]=1[CH:11]=[N:12][C:13]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)=[N:14]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 587119432-(Methyloxy)-n[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamide2×

Product 1

HCID 112684335-methyl-7-[2-(methyloxy)phenyl]-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amineYield 15.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Applying the Cyclization Procedure 1, 2-(methyloxy)-N[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamide (Intermediate 51) (145 mg, 0.38 mmol), 1,2-dichloroethane (4.5 mL) and phosphorus oxychloride (0.285+0.178 mL, 4.97 mmol), to afford 5-methyl-7-[2-(methyloxy)phenyl]-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (21 mg) as a yellow solid. MS m/z 362 (M+1).

Sources & evidence

ORD record
ord-a682c2a005f64d738995f095afe661b8
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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