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

HRID 2374969Notes

Reaction equation

HRID 2374969 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH:10]([C:12]2[N:17]=[N:16][C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:14][CH:13]=2)[CH3:11])=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>ClCCCl>[Br:1][C:2]1[S:6][C:5]([C:7]2[N:17]3[C:12]([CH:13]=[N:14][C:15]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)=[N:16]3)=[C:10]([CH3:11])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 587119305-bromo-N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]-2-thiophenecarboxamide2×

Product 1

HCID 112122007-(5-bromo-2-thienyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amineYield 24%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Applying the Cyclization Procedure 1, using 5-bromo-N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]-2-thiophenecarboxamide (Intermediate 48) (106 mg, 0.24 mmol), 1,2-dichloroethane (5 mL) and phosphorus oxychloride (0.182 mL, 1.95 mmol), to afford 7-(5-bromo-2-thienyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (24 mg) as a yellow solid. MS m/z 416/418 (M+1).

Sources & evidence

ORD record
ord-d282c2fbce664c4082a120c3976610f9
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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