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

HRID 2374871Notes

Reaction equation

HRID 2374871 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([NH:8][CH:9]([C:11]2[N:16]=[N:15][C:14]([NH:17][C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=3)=[N:13][CH:12]=2)[CH3:10])=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>ClCCCl>[F:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]2[N:16]3[C:11]([CH:12]=[N:13][C:14]([NH:17][C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)=[N:15]3)=[C:9]([CH3:10])[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 587120114-fluoro-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide2×

Product 1

HCID 111890407-(4-fluorophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amineYield 15.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a similar manner as described for Example 1, 4-fluoro-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (Intermediate 13) (0.16 g, 0.37 mmol) in 1,2-dichloroethane (20 mL) and phosphorus oxychloride (0.28 mL, 3.0 mmol) gave 7-(4-fluorophenyl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (0.024 g) as a yellow solid. 1H NMR (CDCl3): δ8.78 (s, 1H), 8.50-8.42 (m, 2H), 7.17-7.10 (m, 2H), 7.01 (s, 1H), 6.86 (s, 2H), 3.85 (s, 3H), 3.82 (s, 6H), 2.58 (s, 3H). MS m/z 410 (M+1).

Sources & evidence

ORD record
ord-3707784bbc75414e81772150ca436e27
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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