Acetic Acid → HCID 46831222, compound

HRID 1848359Notes

Reaction equation

HRID 1848359 reaction equation
[CH:1]1([C:4]2[N:22]=[C:7]3[C:8]([O:20][CH3:21])=[CH:9][CH:10]=[C:11]([C:12](=O)[CH:13]([CH3:18])[CH2:14][C:15](O)=[O:16])[N:6]3[N:5]=2)[CH2:3][CH2:2]1.CC(O)=O.[NH2:27][NH2:28]>CCO>[CH:1]1([C:4]2[N:22]=[C:7]3[C:8]([O:20][CH3:21])=[CH:9][CH:10]=[C:11]([C:12]4[CH:13]([CH3:18])[CH2:14][C:15](=[O:16])[NH:27][N:28]=4)[N:6]3[N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9321HydrazineHCID 66707523HCID 66707523, compound

Product 1

HCID 46831222HCID 46831222, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under an argon atmosphere 4-(2-Cyclopropyl-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-5-yl)-3-methyl-4-oxo-butyric acid (0.1 g, ca. 0.33 mmol) was dissolved in EtOH (1.5 mL). AcOH (0.11 mL, 1.98 mmol) and NH2NH2*H2O (0.048 mL, 0.99 mmol) were added. The solution was heated at reflux for 17 h after which it was concentrated in vacuo and co-concentrated with toluene. Aq. NaHCO3 was added and the aqueous phase was extracted with ÉtOAc (×2). The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using EtOAc as the eluent to afford the title compound as a solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 17 h after which it
  3. concentrationwas concentrated in vacuo and co-concentrated with toluene
  4. additionAq. NaHCO3 was added
  5. extractionthe aqueous phase was extracted with ÉtOAc (×2)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-17c545fd541644129391497e95e5e44e
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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