Acetic Acid → HCID 67401630, compound

HRID 1186301Notes

Reaction equation

HRID 1186301 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.[C:24]1([S:30]([NH2:33])(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CS(C)=O>[F:15][C:14]([F:17])([F:16])[CH:13]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)[O:12][C:11]1[C:2]([NH:33][S:30]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:32])=[O:31])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7370BenzenesulfonamideHCID 11430Potassium CarbonateHCID 86657923HCID 86657923, compound

Product 1

HCID 67401630HCID 67401630, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

2-Chloro-3-[2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy]-quinoxaline (Compound BJ) (73 mg, 0.21 mmol) was dissolved in dimethyl sulfoxide (2 mL). To this, benzenesulfonamide (33 mg, 0.21 mmol) and potassium carbonate (29 mg, 0.21 mmol) were added at room temperature and the mixture was stirred at 150° C. for 2 hours. The reaction mixture was allowed to cool down to room temperature, a 1% aqueous acetic acid solution (20 mL) was added thereto, and the precipitate was collected by filtration. The obtained solid was subjected to slurry purification using methanol, to give N-{3-[2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy]quinoxalin-2-yl}benzenesulfonamide (Compound 137) (31 mg, 320).

Workup

  1. temperatureto cool down to room temperature
  2. filtrationthe precipitate was collected by filtration
  3. custompurification

Sources & evidence

ORD record
ord-228268833ea34c4da19024aeb2c6be21
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

Loading…