Sodium Carbonate → 6-[5-benzyloxy-2-(2,2,2-trifluoroethoxy)benzamidomethyl]-2(1H)-pyridone

HRID 542264Notes

Reaction equation

HRID 542264 reaction equation
Br.[NH2:2][CH2:3][C:4]1[NH:9][C:8](=[O:10])[CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:17]([O:24][C:25]1[CH:26]=[CH:27][C:28]([O:34][CH2:35][C:36]([F:39])([F:38])[F:37])=[C:29]([CH:33]=1)[C:30](Cl)=[O:31])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([O:24][C:25]1[CH:26]=[CH:27][C:28]([O:34][CH2:35][C:36]([F:37])([F:39])[F:38])=[C:29]([CH:33]=1)[C:30]([NH:2][CH2:3][C:4]1[NH:9][C:8](=[O:10])[CH:7]=[CH:6][CH:5]=1)=[O:31])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 130371795-Benzyloxy-2-(2,2,2-trifluoroethoxy)benzoyl chlorideHCID 135635896-(Aminomethyl)pyridin-2(1H)-one hydrobromide

Product 1

HCID 135635916-[5-benzyloxy-2-(2,2,2-trifluoroethoxy)benzamidomethyl]-2(1H)-pyridone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Conditions

Temperature
20 °C

Procedure

To a stirred mixture of the crude product from Example 3, 20 ml of acetone and 4.7 g of sodium carbonate was added dropwise 2.8 g (8.21 mmole) of 5-benzyloxy-2-(2,2,2-trifluoroethoxy)benzoyl chloride in 10 ml of acetone. The mixture was stirred at about 20° C. for about 16 hours. To the mixture was added 50 ml of acetone, and the resulting inorganic residue was separated by filtration and washed with acetone. The filtrate and washings were combined and evaporated. This residue was dissolved in benzene, and the solution was washed sequentially with 10% aqueous sodium carbonate solution, 2% acetic acid, water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic solution was dried over magnesium sulfate, and then filtered and evaporated. The residue was boiled in carbon tetrachloride, and the mixture was cooled and the solid was separated by filtration. The solid was purified by chromatography on 30 g of silica gel. The column was eluted sequentially with 5% ethyl acetate in dichloromethane and 2% methanol in dichloromethane. The product was obtained as a white solid, 6-[5-benzyloxy-2-(2,2,2-trifluoroethoxy)benzamidomethyl]-2(1H)-pyridone. The structural assignment was supported by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. customthe resulting inorganic residue was separated by filtration
  2. washwashed with acetone
  3. customevaporated
  4. dissolutionThis residue was dissolved in benzene
  5. washthe solution was washed sequentially with 10% aqueous sodium carbonate solution, 2% acetic acid, water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialThe organic solution was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. temperaturethe mixture was cooled
  10. customthe solid was separated by filtration
  11. customThe solid was purified by chromatography on 30 g of silica gel
  12. washThe column was eluted sequentially with 5% ethyl acetate in dichloromethane and 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-44f4b4bfa2fb457f90f570ade22dba1d
Source dataset
uspto-grants-1987_04
Patent number
US04656285

Reaction notes

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