Ethylene Glycol → HCID 58118937, compound

HRID 1846965Notes

Reaction equation

HRID 1846965 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-5f52cf7f1a9e4870b76a3e02e484c5cd
Source dataset
uspto-grants-2015_02
Patent number
US08952034B2

Reaction notes

Loading…