1H-1,2,4-Triazole → HCID 11752796, compound

HRID 2374930Notes

Reaction equation

HRID 2374930 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:39]=[CH:38][CH:37]=[CH:36][C:11]=1[C:12]([NH:14][CH:15]([C:17]1[N:22]=[N:21][C:20]([NH:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=2)=[N:19][CH:18]=1)[CH3:16])=O)#[N:2].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[S:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]#[N: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 58712010HCID 58712010, compound2×

Product 1

HCID 11752796HCID 11752796, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, 2-[(2-cyanophenyl)thio]-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (Intermediate 39) (269 mg, 0.49 mmol), and 1,2,4-triazole (210 mg, 2.94 mmol) in pyridine (3 mL) and phosphorous oxychloride (0.14 mL, 1.5 mmol) gave 2-[(2-{5-methyl-2-[(3,4,5-trimethoxyphenyl)amino]imidazo[5,1-f][1,2,4]triazin-7-yl}phenyl)thio]benzonitrile (95 mg, 37%) as a yellow solid. 1H NMR (CDCl3): δ8.77 (s, 1H), 7.70 (m, 1H), 7.57 (m, 1H), 7.42-7.47 (m, 3H), 7.10-7.23 (m, 3H), 6.85 (s, 1H), 6.79 (s, 2H), 3.80 (s, 3H), 3.63 (s, 6H), 2.57 (s, 3H). MS m/z 524 (M+1).

Sources & evidence

ORD record
ord-c6cdf323139848a5951327d40d9063e4
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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