1H-1,2,4-Triazole → 5,7-Dimethyl-2-(3-nitrophenyl)-4-(1H-1,2,4-triazol-1-yl)imidazo[5,1-f][1,2,4]triazine

HRID 1270304Notes

Reaction equation

HRID 1270304 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[N:8]=[C:9]([CH3:26])[N:10]2[C:15]=1[C:14](=O)[NH:13][C:12]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)=[N:11]2.[NH:27]1[CH:31]=[N:30][CH:29]=[N:28]1>N1C=CC=CC=1>[CH3:6][C:7]1[N:8]=[C:9]([CH3:26])[N:10]2[C:15]=1[C:14]([N:27]1[CH:31]=[N:30][CH:29]=[N:28]1)=[N:13][C:12]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=1)=[N:11]2

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 24813Phosphorus oxychlorideHCID 1361346445,7-Dimethyl-2-(3-nitrophenyl)imidazo[5,1-f][1,2,4]triazin-4-(3H)one

Product 1

HCID 184491105,7-Dimethyl-2-(3-nitrophenyl)-4-(1H-1,2,4-triazol-1-yl)imidazo[5,1-f][1,2,4]triazine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.35 g (15.35 mmol) of phosphoryl chloride are added dropwise under argon to a solution of 1.46 g (5.12 mmol) of 5,7-dimethyl-2-(3-nitrophenyl)imidazo-[5,1-f][1,2,4]triazin-4-(3H)one from example 9A in 50 ml of dry pyridine at 0° C. and the mixture is stirred for 30 min at RT. Subsequently, 3.18 g (46.06 mmol) of 1,2,4-triazole are added, and the mixture is stirred for 3 h at 20° C. The reaction mixture is concentrated, the residue is treated with aqueous sodium hydrogencarbonate solution and the mixture is extracted with dichloromethane. The organic phase is dried (sodium sulfate) and the solvent is removed in vacuo. The residue is purified by flash chromatography (eluent: dichloromethane/methanol 100:1).

Workup

  1. stirringthe mixture is stirred for 3 h at 20° C
  2. concentrationThe reaction mixture is concentrated
  3. additionthe residue is treated with aqueous sodium hydrogencarbonate solution
  4. extractionthe mixture is extracted with dichloromethane
  5. dry with materialThe organic phase is dried (sodium sulfate)
  6. customthe solvent is removed in vacuo
  7. customThe residue is purified by flash chromatography (eluent: dichloromethane/methanol 100:1)

Sources & evidence

ORD record
ord-970f68c1119e46bbadba9ad34958614e
Source dataset
uspto-grants-2007_04
Patent number
US07202243B2

Reaction notes

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