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

HRID 2374867Notes

Reaction equation

HRID 2374867 reaction equation
[N+:1]([C:4]1[CH:33]=[CH:32][CH:31]=[CH:30][C:5]=1[C:6]([NH:8][CH:9]([C:11]1[N:16]=[N:15][C:14]([NH:17][C:18]2[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=2)=[N:13][CH:12]=1)[CH3:10])=O)([O-:3])=[O:2].P(Cl)(Cl)(Cl)=O>ClCCCl>[CH3:10][C:9]1[N:8]=[C:6]([C:5]2[CH:30]=[CH:31][CH:32]=[CH:33][C:4]=2[N+:1]([O-:3])=[O:2])[N:16]2[C:11]=1[CH:12]=[N:13][C:14]([NH:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=1)=[N:15]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 587119782-nitro-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide2×

Product 1

HCID 112934915-methyl-7-(2-nitrophenyl)-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amineYield 0.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a similar manner as described for Example 1, 2-nitro-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (Intermediate 10) (0.50 g, 1.5 mmol) in 1,2-dichloroethane (20 mL) and phosphorus oxychloride (1.1 mL, 12 mmol) gave 5-methyl-7-(2-nitrophenyl)-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (0.0046 g) as a yellow solid. 1H NMR (CDCl3): δ8.82 (s, 1H), 8.09 (dd, J=8.0, 1.1 Hz, 1H), 7.90 (dd, J=7.7, 1.3 Hz, 1H), 7.76 (ddd, J=7.7, 7.5, 1.3 Hz, 1H), 7.64 (ddd, J=8.2, 7.5, 1.5 Hz, 1H), 6.89 (s, 1H), 6.67 (s, 2H), 3.79 (s, 3H), 3.66 (s, 6H), 2.63 (s, 3H). MS m/z 437 (M+1).

Sources & evidence

ORD record
ord-cd9b76f07c2e429b8fb251ee32a1b50b
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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