Phosphorus oxychloride → 5-methyl-7-[3-(methyloxy)phenyl]-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine

HRID 2374977Notes

Reaction equation

HRID 2374977 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][CH:28]=1)[C:6]([NH:8][CH:9]([C:11]1[N:16]=[N:15][C:14]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[N:13][CH:12]=1)[CH3:10])=O.P(Cl)(Cl)(Cl)=O>ClCCCl>[CH3:10][C:9]1[N:8]=[C:6]([C:5]2[CH:26]=[CH:27][CH:28]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:16]2[C:11]=1[CH:12]=[N:13][C:14]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)=[N:15]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 587119353-(methyloxy)-N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamide2×

Product 1

HCID 111875635-methyl-7-[3-(methyloxy)phenyl]-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amineYield 30.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Applying the Cyclization Procedure 1, 3-(methyloxy)-N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamide (Intermediate 52) (41 mg, 0.11 mmol), 1,2-dichloroethane (2.2 mL) and phosphorus oxychloride (0.081 mL, 0.87 mmol), to afford 5-methyl-7-[3-(methyloxy)phenyl]-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (12 mg) as a yellow solid. MS m/z 362 (M+1).

Sources & evidence

ORD record
ord-738d3911bd7c4d188d4f27ab0288b078
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

Loading…