Phosphorus oxychloride → HCID 11395918, compound

HRID 2374879Notes

Reaction equation

HRID 2374879 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:30]=[CH:31][CH:32]=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)#[N:2].P(Cl)(Cl)(Cl)=O>ClCCCl>[CH3:10][C:9]1[N:8]=[C:6]([C:5]2[CH:4]=[C:3]([CH:32]=[CH:31][CH:30]=2)[C:1]#[N: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 58711974HCID 58711974, compound

Product 1

HCID 11395918HCID 11395918, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a similar manner as described for Example 1,3-cyano-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (Intermediate 17) (0.12 g, 0.25 mmol) in 1,2-dichloroethane (20 mL) and phosphorus oxychloride (0.28 mL, 3.0 mmol) gave 3-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]-imidazo[5,1-f][1,2,4]triazin-7-yl}benzonitrile (0.023 g) as a yellow solid. 1H NMR (CDCl3): δ8.84 (s, 1H), 8.79 (d, J=8.1 Hz, 1H), 8.74 (s, 1H), 7.64 (d, J=7.9 Hz, 1H), 7.54 (dd, J=7.9, 7.8 Hz, 1H) 7.09 (s, 1H), 6.83 (s, 2H), 3.85 (s, 3H), 3.81 (s, 6H), 2.60 (s, 3H). MS m/z 417 (M+1).

Sources & evidence

ORD record
ord-e8c94e9ba2da4e1d89584ea1ebad38fa
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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