Sodium Bicarbonate → HCID 178474043, compound

HRID 392586Notes

Reaction equation

HRID 392586 reaction equation
[OH:1][C:2]([C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([NH:40][C:41](=[O:43])[CH3:42])[CH:34]=[CH:33]2)([C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1)[CH:3]([CH3:5])[CH3:4].Cl.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>CO>[OH:1][C:2]([C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([NH:40][C:41](=[O:43])[CH3:42])[CH:34]=[CH:33]2)([C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)[CH:3]([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 22018433HCID 22018433, compound

Product 1

HCID 178474043HCID 178474043, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

N-{6-[1-Hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]naphthalen-2-yl}acetamide (11.5 g) and pyridine hydrochloride (390 mg) were dissolved in methanol (8 ml) and the mixture was stirred at 60° C. for 2 h. After allowing to cool, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate. The solvent was evaporated and the residue was collected by filtration and washed with ethanol. The filtrate was concentrated and the obtained residue was purified by silica gel column chromatography (eluate, dichloromethane:methanol =30:1→10:1) and recrystallized from ethyl acetate to give the title compound (5.52 g) as a pale-red powder.

Workup

  1. temperatureto cool
  2. customThe solvent was evaporated
  3. filtrationthe residue was collected by filtration
  4. washwashed with ethanol
  5. concentrationThe filtrate was concentrated
  6. customthe obtained residue was purified by silica gel column chromatography (eluate, dichloromethane:methanol =30:1→10:1)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-1cd844a03f744ff7be025c69766b4d69
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

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