1H-1,2,4-Triazole → HCID 11432818, compound

HRID 2374932Notes

Reaction equation

HRID 2374932 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([NH:9][C:10]2[CH:39]=[CH:38][CH:37]=[CH:36][C:11]=2[C:12]([NH:14][CH:15]([C:17]2[N:22]=[N:21][C:20]([NH:23][C:24]3[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=3)=[N:19][CH:18]=2)[CH3:16])=O)[CH:6]=[CH:7][CH:8]=1.N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:16][C:15]1[N:14]=[C:12]([C:11]2[CH:36]=[CH:37][CH:38]=[CH:39][C:10]=2[NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:41])([F:40])[F:1])[CH:4]=2)[N:22]2[C:17]=1[CH:18]=[N:19][C:20]([NH:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=1)=[N:21]2

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 58711972HCID 58711972, compound2×

Product 1

HCID 11432818HCID 11432818, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, 2-{[3-(trifluoromethyl)phenyl]amino}-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (Intermediate 40) (276 mg, 0.48 mmol), and 1,2,4-triazole (200 mg, 2.91 mmol) in pyridine (3 mL) and phosphorous oxychloride (0.14 mL, 1.5 mmol) gave 5-methyl-7-(2-{[3-(trifluoromethyl)phenyl]amino}phenyl)-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (124 mg, 48%) as a yellow solid. 1H NMR (CDCl3): δ9.53 (s, 1H), 8.83 (s, 1H), 8.39 (dd, J=7.87 and 1.28 Hz, 1H), 7.45 (d, J=8.06 Hz, 1H), 7.32 (t, J=7.78 Hz, 2H), 7.23 (m, 2H), 7.12 (d, J=7.51 Hz, 1H), 7.01 (t, J=7.32 Hz, 1H), 6.92 (s, 1H), 6.90 (s, 2H), 3.83 (s, 3H), 3.79 (s, 6H), 2.63 (s, 3H). MS m/z 550 (M+1).

Sources & evidence

ORD record
ord-397655fcd6a8447cae72174d8e87a15c
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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