Pyridinium chloride → HCID 178437261, compound

HRID 1368547Notes

Reaction equation

HRID 1368547 reaction equation
[CH:1]([C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:15]([C:20]1[N:21]=[CH:22][N:23](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:24]=1)([OH:19])[CH:16]([CH3:18])[CH3:17])=[CH:8]2)=[CH2:2].Cl.N1C=CC=CC=1>CO.C1COCC1>[CH:1]([C:3]1[C:12]([O:13][CH3:14])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:15]([C:20]1[N:21]=[CH:22][NH:23][CH:24]=1)([OH:19])[CH:16]([CH3:18])[CH3:17])=[CH:8]2)=[CH2:2]

Participants

5

Reactant 2

HCID 10176127Pyridinium chlorideHCID 220183661-(5-Ethenyl-6-methoxynaphthalen-2-yl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol

Product 1

HCID 178437261HCID 178437261, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1-(5-Ethenyl-6-methoxynaphthalen-2-yl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol (230 mg) was dissolved in a mixed solution of methanol and THF (3:1, 20 ml). To the solution was added pyridine hydrochloride (0.12 g), and the mixture was stirred at 60° C. for 3 h. The reaction mixture was concentrated to dryness, and to the residue were added ethyl acetate and 1N-hydrochloric acid (10 ml). The organic layer was extracted four times with 1N-hydrochloric acid. The aqueous layer was neutralized with an aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried and concentrated. The residue was purified by silica gel chromatography (eluent, dichloromethane-methanol=10:1) to give the titled compound (91 mg).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. additionto the residue were added ethyl acetate and 1N-hydrochloric acid (10 ml)
  3. extractionThe organic layer was extracted four times with 1N-hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium chloride solution
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (eluent, dichloromethane-methanol=10:1)

Sources & evidence

ORD record
ord-81070ba029d64abb9737b0145c9fefbf
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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