1H-1,2,4-Triazole → HCID 11751149, compound

HRID 2374924Notes

Reaction equation

HRID 2374924 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([NH:13][CH:14]([C:16]2[N:21]=[N:20][C:19]([NH:22][C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)=[N:18][CH:17]=2)[CH3:15])=O)=[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:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=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 58711961HCID 58711961, compound2×

Product 1

HCID 11751149HCID 11751149, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, 1-methyl-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)-1H-indole-3-carboxamide (Intermediate 36) (180 mg, 0.39 mmol), and 1,2,4-triazole (165 mg, 2.34 mmol) in pyridine (3 mL) and phosphorous oxychloride (0.11 mL, 1.2 mmol) gave 5-methyl-7-(1-methyl-1H-indol-3-yl)-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amine (102 mg, 59%) as a yellow solid. 1H NMR (DMSO-d6): δ9.47 (s, 1H), 9.16 (s, 1H), 8.52 (d, J=7.87 Hz, 1H), 8.40 (s, 1H), 7.54 (d, J=8.06 Hz, 1H), 7.28 (t, J=7.23 Hz, 1H), 7.20 (t, J=7.42 Hz, 1H), 7.11 (s, 2H), 3.86 (s, 3H), 3.74 (s, 6H), 3.67 (s, 3H), 2.57 (s, 3H). MS m/z 444 (M+1).

Sources & evidence

ORD record
ord-d022740a252e4c3b9be21f7dc314eb8d
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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