Triethyloxonium tetrafluoroborate → HCID 59351576, compound

HRID 1889405Notes

Reaction equation

HRID 1889405 reaction equation
[CH2:1]([C:3]1[S:26][C:6]2[N:7]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([C:18]4[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:14][CH:13]=3)[C:8](=[O:10])[NH:9][C:5]=2[CH:4]=1)[CH3:2].F[B-](F)(F)F.[CH2:32]([O+](CC)CC)[CH3:33]>O1CCOCC1>[CH2:32]([O:10][C:8]1[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:24]#[N:25])=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:14][CH:13]=2)[C:6]2[S:26][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=2[N:9]=1)[CH3:33]

Participants

4

Reactant 2

HCID 2723982Triethyloxonium tetrafluoroborateHCID 59351757HCID 59351757, compound

Product 1

HCID 59351576HCID 59351576, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 4′-[(5-ethyl-2-oxo-1,2-dihydro-3H-thieno[2,3-d]imidazol-3-yl)methyl]biphenyl-2-carbonitrile (0.5 g) and 1,4-dioxane was added triethyloxonium tetrafluoroborate (1M methylene chloride solution, 4.2 mL), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was extracted with chloroform and water. The obtained chloroform layer was successively washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.48 g, 92%).

Workup

  1. extractionThe reaction mixture was extracted with chloroform and water
  2. washThe obtained chloroform layer was successively washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-04359960cf114adc96225abc14007928
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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