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

HRID 2374979Notes

Reaction equation

HRID 2374979 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[C:4]([NH:6][CH:7]([C:9]1[N:14]=[N:13][C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[N:11][CH:10]=1)[CH3:8])=O.P(Cl)(Cl)(Cl)=O>ClCCCl>[Cl:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[C:4]1[N:14]2[C:9]([CH:10]=[N:11][C:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[N:13]2)=[C:7]([CH3:8])[N:6]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 587119932-chloro-N-(1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamide2×

Product 1

HCID 111527797-(2-chlorophenyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amineYield 32.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Applying the Cyclization Procedure 1, 2-chloro-N-[1-(3-{[4-(methyloxy)phenyl]amino}-1,2,4-triazin-6-yl)ethyl]benzamide (Intermediate 53) (127 mg, 0.33 mmol), 1,2-dichloroethane (6.6 mL) and phosphorus oxychloride (0.250+0.154 mL, 4.33 mmol), to afford 7-(2-chlorophenyl)-5-methyl-N-[4-(methyloxy)phenyl]imidazo[5,1-f][1,2,4]triazin-2-amine (39 mg) as a yellow solid. MS m/z 366 (M+1).

Sources & evidence

ORD record
ord-1790bc4ac70e46b2933dfdd83252e671
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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