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

HRID 2374869Notes

Reaction equation

HRID 2374869 reaction equation
[Br:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][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]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)=[N:11][CH:10]=1)[CH3:8])=O.P(Cl)(Cl)(Cl)=O>ClCCCl>[Br:1][C:2]1[CH:31]=[CH:30][CH:29]=[CH:28][C:3]=1[C:4]1[N:14]2[C:9]([CH:10]=[N:11][C:12]([NH:15][C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)=[N:13]2)=[C:7]([CH3:8])[N:6]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 587120052-bromo-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide2×

Product 1

HCID 112943487-(2-bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amineYield 1.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a similar manner as described for Example 1, 2-bromo-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (Intermediate 12) (0.45 g, 0.92 mmol) in 1,2-dichloroethane (20 mL) and phosphorus oxychloride (0.69 mL, 7.4 mmol) gave 7-(2-bromophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (0.0069 g) as a yellow solid. 1H NMR (CDCl3): δ8.85 (s, 1H), 7.67 (d, J=7.9 Hz, 1H), 7.58 (dd, J=7.6, 1.4 Hz, 1H), 7.44 (dd, J=7.7, 7.3 Hz, 1H), 7.35 (ddd, J=7.9, 7.7, 1.4 Hz, 1H), 6.99 (s, 1H), 6.83 (s, 2H), 3.78 (s, 3H), 3.62 (s, 6H), 2.64 (s, 3H). MS m/z 470, 472 (M+1, M+3).

Sources & evidence

ORD record
ord-59526920c1a641a5aca8ccbf95b2011d
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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