1H-1,2,4-Triazole → HCID 135545443, compound

HRID 2374918Notes

Reaction equation

HRID 2374918 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[NH:26][C:27]4[C:32]([CH:33]=3)=[CH:31][CH: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:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:33]=[C:25]1[C:23]1[N:16]2[C:17]([CH:18]=[N:19][C:14]([NH:13][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)=[N:15]2)=[C:20]([CH3:21])[N:22]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 58711990HCID 58711990, compound2×

Product 1

HCID 135545443HCID 135545443, compoundYield 61%

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-2-carboxamide (Intermediate 33) (219 mg, 0.491 mmol), and 1,2,4-triazole (210 mg, 3.0 mmol) in pyridine (10 mL) and phosphorous oxychloride (0.14 mL, 1.5 mmol) gave 7-(1H-indol-2-yl)-5-methyl-N-(3,4,5-trimethoxyphenyl)imidazo[5,1-f][1,2,4]triazin-2-amine (128 mg, 61%) as a yellow solid: 1H NMR (DMSO-d6): δ11.85 (s, 1H), 9.67 (s, 1H), 9.26 (s, 1H) 7.55 (s, 1H), 7.52 (d, J=8.24 Hz, 1H), 7.46 (d, J=8.24 Hz, 1H), 7.21 (s, 2H), 7.15 (t, J=7.51, 1H), 7.04 (t, J=7.51 Hz, 1H), 3.82 (s, 6H), 3.68 (s, 3H), 2.58 (s, 3H). MS m/z 430 (M+1).

Sources & evidence

ORD record
ord-03452741edd54d0382661fb04150fd27
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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