Pyridinium chloride → HCID 178487496, compound

HRID 1368531Notes

Reaction equation

HRID 1368531 reaction equation
[Si:1]([O:8][CH:9]([C:11]1[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15]([C:23]([C:25]1[N:26]=[CH:27][NH:28][CH:29]=1)=[O:24])=[CH:16]2)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si](OC(C1C(OC)=CC=C2C=1C=CC(C(C1N=CN(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)C=1)=O)=C2)C)([C:33](C)([CH3:35])[CH3:34])(C)C.Cl.N1C=CC=CC=1>CO>[Si:1]([O:8][CH:9]([C:11]1[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15]([C:23]([C:25]1[N:26]=[CH:27][NH:28][CH:29]=1)([OH:24])[CH:33]([CH3:35])[CH3:34])=[CH:16]2)[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10176127Pyridinium chlorideHCID 22018331[5-[1-(tert-butyldimethylsilyloxy)ethyl]-6-methoxynaphthalen-2-yl]-(1-trityl-1H-imidazol-4-yl)ketoneHCID 178487491HCID 178487491, compound

Product 1

HCID 178487496HCID 178487496, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Production of [5-[1-(tert-Butyldimethylsilyloxy)-ethyl]-6-methoxynaphthalen-2-yl]-(1H-imidazol-4-yl)ketone. [5-[1-(tert-butyldimethylsilyloxy)ethyl]-6-methoxynaphthalen-2-yl]-(1-trityl-1H-imidazol-4-yl)ketone (5.18 g) and pyridine hydrochloride (1.59 g) were dissolved in methanol (50 ml). The solution was stirred at 50° C. for 1 h. The reaction mixture was concentrated, and water and ethyl acetate were added. The organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate and saturated sodium chloride solution, dried and concentrated. The obtained residue was washed with ether to give the titled compound (2.71 g) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater and ethyl acetate were added
  3. washThe organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate and saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. washThe obtained residue was washed with ether

Sources & evidence

ORD record
ord-cc76b22b44bc46febbdbff6215b3fc29
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

Loading…