Dimethyl Sulfoxide → HCID 86657924, compound

HRID 1186303Notes

Reaction equation

HRID 1186303 reaction equation
Cl[C:2]1[C:11]([O:12][CH:13]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:14]([F:17])([F:16])[F:15])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.CS(C)=O.[F:28][C:29]([F:35])([F:34])[S:30]([NH2:33])(=[O:32])=[O:31].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[F:28][C:29]([F:35])([F:34])[S:30]([NH:33][C:2]1[C:11]([O:12][CH:13]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:14]([F:17])([F:16])[F:15])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)(=[O:32])=[O:31]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 79001TrifluoromethylsulfonamideHCID 86657923HCID 86657923, compound

Product 1

HCID 86657924HCID 86657924, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

According to Example 132, by use of 2-chloro-3-[2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy]-quinoxaline (Compound BJ) (70 mg, 0.21 mmol), dimethyl sulfoxide (2 mL), trifluoromethanesulfonamide (31 mg, 0.21 mmol) and potassium carbonate (28 mg, 0.21 mmol), the mixture was stirred and reacted at 150° C. for 1.5 hours. The reaction mixture was allowed to cool down to room temperature, a 1% aqueous acetic acid solution was added thereto, and extraction with ethyl acetate was performed. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and then the solvent was evaporated off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 20/1). Further, slurry purification was performed using isopropyl ether, to give 1,1,1-trifluoro-N-{3-[2,2,2-trifluoro-1-(pyridin-3-yl)-ethoxy]quinoxalin-2-yl}methanesulfonamide (Compound 149) (13 mg, 14%).

Workup

  1. customreacted at 150° C. for 1.5 hours
  2. extractionextraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 20/1)
  7. customFurther, slurry purification

Sources & evidence

ORD record
ord-b1ddb4e7b8434c85995a33bab106149f
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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