Ethylene Glycol → HCID 58118937, compound

HRID 406453Notes

Reaction equation

HRID 406453 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[N:7]2[CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=3)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.[CH2:23](O)[CH2:24][OH:25].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[CH3:19][C:18]1([C:15]2[CH:16]=[CH:17][C:12]([C:9]3[CH:10]=[CH:11][C:6]4[N:7]([C:3]([C:2]([F:1])([F:21])[F:22])=[N:4][N:5]=4)[CH:8]=3)=[CH:13][CH:14]=2)[O:25][CH2:24][CH2:23][O:20]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 58118946HCID 58118946, compound

Product 1

HCID 58118937HCID 58118937, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 50-mL round-bottom flask equipped with a magnetic stir bar 1-(4-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)phenyl)ethanone (50 mg) was dissolved in dry toluene (1 mL), ethylene glycol (0.1 mL) and camphorsulfonic acid (a few crystals) were added. The reaction mixture was stirred overnight at reflux temperature. Extracted with concentrated NaHCO3 and EtOAc, organic layer dried over MgSO4, concentrated, and purified by chromatography (1:1 hexanes/EtOAc). The desired 6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine was isolated.

Workup

  1. temperatureat reflux temperature
  2. extractionExtracted with concentrated NaHCO3 and EtOAc, organic layer
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified by chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-26345ff496db4e819a89817156624e53
Source dataset
uspto-grants-2014_06
Patent number
US08754103B2

Reaction notes

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