1H-1,2,4-Triazole → HCID 11396293, compound

HRID 2374928Notes

Reaction equation

HRID 2374928 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]=[C:27]4[C:31](=[CH:32][CH:33]=3)[NH:30][CH:29]=[CH:28]4)=O)[CH3:21])=[CH:18][N:19]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[NH:30]1[C:31]2[C:27](=[CH:26][C:25]([C:23]3[N:16]4[C:17]([CH:18]=[N:19][C:14]([NH:13][C:5]5[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=5)=[N:15]4)=[C:20]([CH3:21])[N:22]=3)=[CH:33][CH:32]=2)[CH:28]=[CH:29]1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 58711975HCID 58711975, compound2×

Product 1

HCID 11396293HCID 11396293, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)-1H-indole-5-carboxamide (Intermediate 38) (176 mg, 0.39 mmol), and 1,2,4-triazole (161 mg, 2.34 mmol) in pyridine (4 mL) and phosphorous oxychloride (0.11 mL, 1.2 mmol) gave 7-(1H-indol-5-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (63 mg, 37%) as a yellow solid. 1H NMR (CDCl3): δ8.87 (s, 1H), 8.79 (s, 1H), 8.35 (s, 1H), 8.29 (dd, J=8.61 and 1.46 Hz, 1H), 7.47 (d, J=8.61 Hz, 1H), 6.95 (s, 2H), 6.84 (s, 1H), 6.62 (s, 1H), 3.87 (s, 3H), 3.77 (s, 6H), 2.64 (s, 3H). MS m/z 430 (M+1).

Sources & evidence

ORD record
ord-e93bbd1f5ab64c0e8fbfd42cfb1b985b
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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