Cesium carbonate → HCID 73776715, compound

HRID 2207280Notes

Reaction equation

HRID 2207280 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=3)[N:10]=[CH:9][C:8]=2[OH:19])[CH:4]=[N:3]1.C([O-])([O-])=O.[Cs+].[Cs+].[C:26]([C:28]1[CH:29]=[C:30]([S:35]([NH:38][C:39]2[S:40][CH:41]=[CH:42][N:43]=2)(=[O:37])=[O:36])[CH:31]=[CH:32][C:33]=1F)#[N:27]>CN(C)C=O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH3:18])[CH:17]=3)[N:10]=[CH:9][C:8]=2[O:19][C:33]2[CH:32]=[CH:31][C:30]([S:35]([NH:38][C:39]3[S:40][CH:41]=[CH:42][N:43]=3)(=[O:36])=[O:37])=[CH:29][C:28]=2[C:26]#[N:27])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 580422683-Cyano-4-fluoro-N-(thiazol-2-yl)benzenesulfonamideHCID 90101670HCID 90101670, compound

Product 1

HCID 73776715HCID 73776715, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 mg (0.04 mmol) of 4,6-bis(1-methyl-1H-pyrazol-4-yl)pyridin-3-ol was dissolved in 3 mL of N,N-dimethylformamide, and 32 mg (0.1 mmol) of Cs2CO3 was added thereto, followed by stirring at room temperature for 10 minutes. Then, 11 mg (0.04 mmol) of 3-cyano-4-fluoro-N-(thiazol-2-yl)benzenesulfonamide was added thereto, and the solution was stirred at room temperature for 3 hours. After completion of the reaction as checked by TLC, the solvent was removed, and the remaining material was diluted with ethyl acetate and washed with saturated sodium chloride. The organic layer was collected, dried with magnesium sulfate to remove water, and concentrated under reduced pressure, and the residue was purified by column chromatography (developing solvent, hexane:ethyl acetate=3:1) to obtain 16.0 mg (80% yield) of the title compound.

Workup

  1. stirringthe solution was stirred at room temperature for 3 hours
  2. customAfter completion of the reaction
  3. customthe solvent was removed
  4. additionthe remaining material was diluted with ethyl acetate
  5. washwashed with saturated sodium chloride
  6. customThe organic layer was collected
  7. dry with materialdried with magnesium sulfate
  8. customto remove water
  9. concentrationconcentrated under reduced pressure
  10. customthe residue was purified by column chromatography (developing solvent, hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-bf3326cc7ba948b390f3c5a09ec004ea
Source dataset
uspto-grants-2016_06
Patent number
US09376429B2

Reaction notes

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