Pyridinium chloride → HCID 178450102, compound

HRID 1059136Notes

Reaction equation

HRID 1059136 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([C:19]3[N:20]=[CH:21][N:22](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:23]=3)([OH:18])[CH:15]([CH3:17])[CH3:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([C:19]3[N:20]=[CH:21][NH:22][CH:23]=3)([OH:18])[CH:15]([CH3:17])[CH3:16])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 120433881-(4'-fluoro[1,1'-biphenyl]-4-yl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol

Product 1

HCID 178450102HCID 178450102, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution (75 ml) of 1-(4′-fluoro[1,1′-biphenyl]-4-yl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol (3.12 g) and pyridine hydrochloride (1.11 g) in methanol was stirred at 60° C. for 3.5 h. The solvent was evaporated from the reaction mixture under reduced pressure and the residue was diluted with ethyl acetate. Saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by column chomatography (eluent, hexane:ethyl acetate=2:1→1:5) and recrystallized from ethyl acetate-hexane to give the title compound (1.34 g) as colorless needle crystals.

Workup

  1. customThe solvent was evaporated from the reaction mixture under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. additionSaturated aqueous sodium hydrogen carbonate was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by column chomatography (eluent, hexane:ethyl acetate=2:1→1:5)
  9. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-dc862e783856401d91e4a77b540fa4b1
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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