Phosphorus oxychloride → HCID 11375509, compound

HRID 2374877Notes

Reaction equation

HRID 2374877 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]([NH:5][C:6]1[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=1[C:8]([NH:10][CH:11]([C:13]1[N:18]=[N:17][C:16]([NH:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=2)=[N:15][CH:14]=1)[CH3:12])=O)=[O:4].P(Cl)(Cl)(Cl)=O>ClCCCl>[F:1][C:2]([F:37])([F:36])[C:3]([NH:5][C:6]1[CH:35]=[CH:34][CH:33]=[CH:32][C:7]=1[C:8]1[N:18]2[C:13]([CH:14]=[N:15][C:16]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=3)=[N:17]2)=[C:11]([CH3:12])[N:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 58711991HCID 58711991, compound2×

Product 1

HCID 11375509HCID 11375509, compoundYield 10.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a similar manner as described for Example 1, 2-[(trifluoroacetyl)amino]-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (Intermediate 16) (0.118 g, 0.23 mmol) in 1,2-dichloroethane (30 mL) and phosphorus oxychloride (1.0 mL, 11 mmol) gave 2,2,2-trifluoro-N-(2-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)acetamide (0.012 g) as a yellow solid. 1H NMR (CDCl3): δ13.87 (s, 1H), 8.91 (dd, J=8.0, 1.4 Hz, 1H), 8.88 (s, 1H), 8.63 (dd, J=8.4, 1.1 Hz, 1H), 7.47-7.41 (m, 1H), 7.28-7.22 (m, 1H), 7.08 (s, 1H), 6.86 (s, 2H), 3.85 (s, 3H), 3.80 (s, 6H), 2.60 (s, 3H). MS m/z 503 (M+1).

Sources & evidence

ORD record
ord-1d4787af7dda4788840857192b3a0711
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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