Tetrahydrofuran → HCID 178504738, compound

HRID 1882075Notes

Reaction equation

HRID 1882075 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[NH:5][C:6]=1/[C:7](/[C:15]1[CH:20]=[CH:19][C:18](SC)=[C:17]([Cl:23])[CH:16]=1)=[CH:8]/[CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.O1CCC[CH2:31]1.O[O:36][S:37]([O-:39])=O.[K+].C(=O)([O-])O.[Na+]>O.CO>[Cl:1][C:2]1[N:3]=[C:4]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)[NH:5][C:6]=1/[C:7](/[C:15]1[CH:20]=[CH:19][C:18]([S:37]([CH3:31])(=[O:39])=[O:36])=[C:17]([Cl:23])[CH:16]=1)=[CH:8]/[CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 178503158HCID 178503158, compound

Product 1

HCID 178504738HCID 178504738, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-{4-chloro-5-[(E)-1-[3-chloro-4-(methylsulfanyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethenyl]-1H-imidazol-2-yl}pyridine (1.10 g) in a mixed solvent of tetrahydrofuran (10 mL), methanol (10 mL) and water (10 mL) was added Oxone (registered trade mark) (3.02 g) under ice-cooling, and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To a solution of the residue in a mixed solvent of acetonitrile (20 mL) and water (10 mL) was added sodium percarbonate (772 mg) under ice-cooling. The reaction solution was warmed to room temperature, and the mixture was stirred at room temperature for 3 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-100:0, volume ratio) to give the title compound (0.471 g, yield 40%) as a colorless amorphous solid. MS: 478 (MH+).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo a solution of the residue in a mixed solvent of acetonitrile (20 mL) and water (10 mL) was added sodium percarbonate (772 mg) under ice-
  7. temperaturecooling
  8. temperatureThe reaction solution was warmed to room temperature
  9. stirringthe mixture was stirred at room temperature for 3 hr
  10. additionA saturated aqueous ammonium chloride solution was added to the reaction mixture
  11. extractionthe mixture was extracted with ethyl acetate
  12. washThe extract was washed successively with water and saturated brine
  13. dry with materialdried over anhydrous sodium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=40:60-100:0, volume ratio)

Sources & evidence

ORD record
ord-4a993614cc3c4dc9b5cf18b95761971b
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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