Trifluoroacetic acid → (3-oxo-6-(1H-1,2,4-triazol-1-yl)pyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehyde

HRID 385647Notes

Reaction equation

HRID 385647 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:12](=[O:13])[CH:11]=[N:10][C:9]2[CH:14]=[CH:15][C:16]([N:18]3[CH:22]=[N:21][CH:20]=[N:19]3)=[N:17][C:8]1=2.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].[OH-].[Na+]>C(OCC)(=O)C.O>[O:13]=[C:12]1[N:7]([CH2:6][CH:2]=[O:1])[C:8]2[N:17]=[C:16]([N:18]3[CH:22]=[N:21][CH:20]=[N:19]3)[CH:15]=[CH:14][C:9]=2[N:10]=[CH:11]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 578152554-(1,3-dioxolan-2-ylmethyl)-6-(1H-1,2,4-triazol-1-yl)pyrido(2,3-b)pyrazin-3(4H)-one

Product 1

HCID 57815520(3-oxo-6-(1H-1,2,4-triazol-1-yl)pyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehydeYield 143.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 98 mg of 4-(1,3-dioxolan-2-ylmethyl)-6-(1H-1,2,4-triazol-1-yl)pyrido(2,3-b)pyrazin-3(4H)-one, 3 mL of an 80% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at room temperature for 6 hours 30 minutes. Thereto were added water and ethyl acetate, and the mixture was neutralized with a saturated aqueous sodium hydrogen carbonate solution and an aqueous sodium hydroxide solution. The organic layer was separated, and sodium chloride was added to the aqueous layer, and the mixture was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.12 g of (3-oxo-6-(1H-1,2,4-triazol-1-yl)pyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehyde as a light red solid.

Workup

  1. customThe organic layer was separated
  2. additionsodium chloride was added to the aqueous layer
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9a534c6f0f4543cf950b61205a4011d0
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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