1H-1,2,4-Triazole → HCID 11155941, compound

HRID 2374914Notes

Reaction equation

HRID 2374914 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:35]=[CH:36][CH:37]=1)[C:11]([NH:13][CH:14]([C:16]1[N:21]=[N:20][C:19]([NH:22][C:23]2[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=2)=[N:18][CH:17]=1)[CH3:15])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:15][C:14]1[N:13]=[C:11]([C:10]2[CH:35]=[CH:36][CH:37]=[C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=2)[N:21]2[C:16]=1[CH:17]=[N:18][C:19]([NH:22][C:23]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=1)=[N:20]2

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 587120003-phenoxy-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide2×

Product 1

HCID 11155941HCID 11155941, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, 3-phenoxy-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (Intermediate 31) (58 mg, 0.11 mmol), and 1,2,4-triazole (55 mg, 0.80 mmol) in pyridine (2 mL) and phosphorous oxychloride (0.037 mL, 0.40 mmol) gave 5-methyl-7-(3-phenoxyphenyl)-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (27 mg, 49%) as a tan-yellow solid. 1H NMR (CD3OD): δ8.99 (s, 1H), 8.08 (d, J=7.87 Hz, 1H), 7.96 (t, J=1.92 Hz), 7.44 (t, J=8.06 Hz, 1H), 7.31 (t, J=7.87 Hz, 2H), 7.00-7.11 (m, 6H), 3.77 (s, 6H), 3.72 (s, 3H), 2.54 (s, 3H). MS m/z 448 (M+1).

Sources & evidence

ORD record
ord-72f6b6701c414c0d9f63f6e1ee3024f0
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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