Potassium Carbonate → HCID 86692800, compound

HRID 339712Notes

Reaction equation

HRID 339712 reaction equation
[F:1][C:2]([F:17])([N:8]1[CH:12]=[CH:11][C:10]([S:13](=[O:16])(=[O:15])[NH2:14])=[N:9]1)[C:3]([N:5]([CH3:7])[CH3:6])=[O:4].[Cl:18][C:19]1[C:28](Cl)=[N:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[Cl:18][C:19]1[C:28]([NH:14][S:13]([C:10]2[CH:11]=[CH:12][N:8]([C:2]([F:1])([F:17])[C:3]([N:5]([CH3:7])[CH3:6])=[O:4])[N:9]=2)(=[O:15])=[O:16])=[N:27][C:26]2[C:21]([N:20]=1)=[CH:22][CH:23]=[CH:24][CH:25]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 166592,3-DichloroquinoxalineHCID 67512417HCID 67512417, compound

Product 1

HCID 86692800HCID 86692800, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

1.30 g of 2,2-difluoro-N,N-dimethyl-2-(3-sulfamoylpyrazol-1-yl)acetamide, 1.16 g of 2,3-dichloroquinoxaline and 670 mg of potassium carbonate in about 16 ml of dried DMA are heated at 100° C. (bath temperature) under nitrogen in a flask until the sulfonamide has reacted virtually completely (HPLC check, about 3 hours). The cooled reaction solution is poured into about 200 ml of ice-water, with a precipitate depositing after some time. This is filtered off with suction and discarded. The filtrate is adjusted to pH 4-5 using saturated citric acid solution. A further precipitate deposits, which is filtered off, washed with water and dried, giving 1.44 g of 2-[3-(3-chloroquinoxalin-2-ylsulfamoyl)pyrazol-1-yl]-2,2-difluoro-N,N-dimethylacetamide as pale-beige solid (yield 69%, content 99.8%). MS-FAB (M+H+)=431.0. Rf (polar method): 1.98 min. This is employed without further purification for the next step.

Workup

  1. customhas reacted virtually completely (HPLC check, about 3 hours)
  2. customThe cooled reaction solution
  3. filtrationThis is filtered off with suction
  4. filtrationA further precipitate deposits, which is filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-05547220a8494cfa9cfc29a3db8f64b7
Source dataset
uspto-grants-2014_11
Patent number
US08895559B2

Reaction notes

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