Ethanol → HCID 86634944, compound

HRID 1952251Notes

Reaction equation

HRID 1952251 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:16][CH:17](Cl)[F:18])[C:10]2[CH2:14][O:13][C:12](=[O:15])[CH:11]=2)=[CH:4][CH:3]=1.[OH-].[K+].[CH2:22](O)C>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH:16]=[CH:17][F:18])[C:10]2[CH:14]([CH3:22])[O:13][C:12](=[O:15])[CH:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 57908393HCID 57908393, compound

Product 1

HCID 86634944HCID 86634944, compoundYield 94%

Procedure

68 mg (0.22 mmol) of 4-[[(6-chloropyridin-3-yl)methyl](2-chloro-2-fluoroethyl)amino]furan-2(5H)-one (17) are initially charged in 5 ml of ethanol, 38 mg (0.67 mmol) of potassium hydroxide are added and the reaction mixture is stirred at room temperature for about 18 hours. The reaction mixture is then partitioned between ethyl acetate and water, and the organic phase is separated off. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (silica gel 60—Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (2:1) gives 57 mg (94% of theory) of 4-[[(6-chloropyridin-3-yl)methyl](2-fluorovinyl)amino]-5-methylfuran-2(5H)-one as an (E/Z) isomer mixture (15:85).

Workup

  1. customThe reaction mixture is then partitioned between ethyl acetate and water
  2. customthe organic phase is separated off
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by column chromatography on silica gel (silica gel 60—Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record
ord-aa1bfeb3fd094938a88c23aa076d39af
Source dataset
uspto-grants-2013_03
Patent number
US08404855B2

Reaction notes

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