Phosphorus oxychloride → HCID 58712007, compound

HRID 2374934Notes

Reaction equation

HRID 2374934 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:13][C:14]2[N:15]=[N:16][C:17]([CH:20]([NH:22][C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[C:29]4[C:34]=3[N:33]=[CH:32][CH:31]=[CH:30]4)=O)[CH3:21])=[CH:18][N:19]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].P(Cl)(Cl)(Cl)=O>ClCCCl>[CH3:21][C:20]1[N:22]=[C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:34]=2[N:33]=[CH:32][CH:31]=[CH:30]3)[N:16]2[C:17]=1[CH:18]=[N:19][C:14]([NH:13][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=1)=[N:15]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 58711932HCID 58711932, compound2×

Product 1

HCID 58712007HCID 58712007, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a similar manner as described for Example 1, N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)quinoline-8-carboxamide (Intermediate 41) (0.080 g, 0.17 mmol) in 1,2-dichloroethane (5 mL) and phosphorus oxychloride (0.13 mL, 1.4 mmol) gave 5-methyl-7-quinolin-8-yl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (0.022 g) as a yellow solid. 1H NMR (CDCl3): δ8.90 (dd, J=4.2, 1.8 Hz, 1H), 8.83 (s, 1H), 8.22 (dd, J=8.3, 1.8 Hz, 1H), 8.03 (dd, J=7.2, 1.5 Hz, 1H), 7.97 (dd, J=8.2, 1.5 Hz, 1H), 7.67 (dd, J=8.2, 7.1 Hz, 1H), 7.45-7.41 (m, 1H), 6.91 (bs, 1H), 6.58 (s, 2H), 3.69 (s, 3H), 3.25 (s, 6H), 2.67 (s, 3H). MS m/z 443 (M+1).

Sources & evidence

ORD record
ord-d6ea75c1f0214cd8a59ef4c48e8b31d3
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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