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

HRID 2374971Notes

Reaction equation

HRID 2374971 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH:9][CH:10]([C:12]1[N:17]=[N:16][C:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[N:14][CH:13]=1)[CH3:11])=O.P(Cl)(Cl)(Cl)=O>ClCCCl>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[N:17]2[C:12]([CH:13]=[N:14][C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[N:16]2)=[C:10]([CH3:11])[N:9]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 587119833-bromo-N-[1-(3-{[4-(methyloxy)phenyl]amino}1,2,4-triazin-6-yl)ethyl]-2-thiophenecarboxamide2×

Product 1

HCID 117743627-(3-bromo-2-thienyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amineYield 22.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Applying the Cyclization Procedure 1, using 3-bromo-N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]-2-thiophenecarboxamide (Intermediate 49) (159 mg, 0.37 mmol), 1,2-dichloroethane (7.3 mL) and phosphorus oxychloride (0.273 mL, 2.93 mmol), to afford 7-(3-bromo-2-thienyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (35 mg) as a yellow solid. MS m/z 416/418 (M+1).

Sources & evidence

ORD record
ord-ec22ffacb55f40759b4db80b6356330c
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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