Acetone → HCID 118205935, compound

HRID 713663Notes

Reaction equation

HRID 713663 reaction equation
CI.[CH2:3]([S:5]([C:8]1[C:9]([C:14]([NH:16][C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=2)=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6])[CH3:4].[C:31](=O)([O-])[O-].[K+].[K+].CC(C)=O>O.CN(C=O)C>[CH2:3]([S:5]([C:8]1[C:9]([C:14]([N:16]([CH3:31])[C:17]2[CH:18]=[C:19]([C:27]([F:30])([F:28])[F:29])[CH:20]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:22]=2)=[O:15])=[N:10][CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6])[CH3:4]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 118113340HCID 118113340, compound

Product 1

HCID 118205935HCID 118205935, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.50 g of methyl iodide was added to a mixture of 0.20 g of 3-ethylsulfonyl-N-(3,5-bistrifluoromethylphenyl)picolinamide (Compound of Present Invention 14), 0.12 g of potassium carbonate and 3 mL of acetone, and the mixture was stirred at room temperature for 1 hour. 1 mL of DMF was added to the reaction mixture, and the mixture was stirred at 60° C. for 2 hours. Water was added to the reaction mixture cooled to room temperature, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.18 g of 3-ethylsulfonyl-N-methyl-N-(3,5-bistrifluoromethylphenyl)picolinamide (hereinafter, referred to as Compound of Present Invention 38).

Workup

  1. stirringthe mixture was stirred at 60° C. for 2 hours
  2. temperaturecooled to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1659f38bdf41404b9d7db5b64b834d5f
Source dataset
uspto-grants-2015_11
Patent number
US09185910B2

Reaction notes

Loading…