1H-1,2,4-Triazole → HCID 135507498, compound

HRID 2374920Notes

Reaction equation

HRID 2374920 reaction equation
[N+:1]([C:4]1[NH:8][C:7]([C:9]([NH:11][CH:12]([C:14]2[N:19]=[N:18][C:17]([NH:20][C:21]3[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=3)=[N:16][CH:15]=2)[CH3:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=NC=N1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:13][C:12]1[N:11]=[C:9]([C:7]2[NH:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:19]2[C:14]=1[CH:15]=[N:16][C:17]([NH:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=1)=[N:18]2

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 58711938HCID 58711938, compound2×

Product 1

HCID 135507498HCID 135507498, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner as described for Example 9, 5-nitro-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)-1H-pyrrole-2-carboxamide (Intermediate 34) (201 mg, 0.45 mmol), and 1,2,4-triazole (190 mg, 2.72 mmol) in pyridine (10 mL) and phosphorous oxychloride (0.13 mL, 1.36 mmol) gave 5-methyl-7-(5-nitro-1H-pyrrol-2-yl)-N-(3,4,5-trimethoxyphenyl)-imidazo[5,1-f][1,2,4]triazin-2-amine (95 mg, 49%) as a yellow solid. 1H NMR (DMSO-d6): δ13.04 (s, 1H), 9.63 (s, 1H), 9.25 (s, 1H), 7.98 (dd, J=3.30 and 1.65 Hz, 1H), 7.57 (t, J=2.01 Hz, 1H), 7.05 (s, 2H), 3.74 (s, 6H), 3.65 (s, 3H), 2.54 (s, 3H). MS m/z 425 (M+1).

Sources & evidence

ORD record
ord-742c43145baf418987c0be0f6032781b
Source dataset
uspto-grants-2008_12
Patent number
US07462614B2

Reaction notes

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