Potassium Carbonate → N-pyrimidinyl piperidine sulfonamide

HRID 392379

Reaction equation

HRID 392379 reaction equation
[N:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])=O.[NH4+].C(=O)([O-])[O-].[K+].[K+].Cl[C:22]1[N:27]=[C:26](C(F)(F)F)[CH:25]=[CH:24][N:23]=1>CO.CN(C)C=O>[N:23]1[CH:24]=[CH:25][CH:26]=[N:27][C:22]=1[NH:10][S:7]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:9])=[O:8]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2767411-PiperidinesulfonamideHCID 2723923Ammonium formateHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidine

Product 1

HCID 22052662N-pyrimidinyl piperidine sulfonamideYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a slurry of the piperidine sulfonamide from part F (6.3 g, 12.0 mmol) in methanol (25 mL) was added ammonium formate (2.2 g, 34.5 mmol). The system was purged with nitrogen for 10 minutes. The nitrogen stream was removed and palladium on carbon (1.2 g of 10 weight % on activated carbon, 50% water) was added. The reaction was refluxed for forty five minutes, cooled, filtered through Celite under nitrogen, and concentrated in vacuo. The residue (4.5 g, 10 mmol) was dissolved in dry dimethylformamide (20 mL) and potassium carbonate (4.14 g, 30 mmol) and 2-chloro-4-trifluoromethylpyrimidine (2.4 mL, 20 mmol) were added. The reaction was stirred at seventy degrees Celsius for three hour and then concentrated in vacuo. The residue was taken up in ethyl acetate and filtered through Celite. The filtrate washed with water two times, saturated sodium chloride solution, dried over Na2SO4, filtered, and concentrated in vacuo. The product was recrystallized (methanol) to give the N-pyrimidinyl piperidine sulfonamide as a white solid (4.51 g, 76%).

Workup

  1. customThe system was purged with nitrogen for 10 minutes
  2. customThe nitrogen stream was removed
  3. additionpalladium on carbon (1.2 g of 10 weight % on activated carbon, 50% water) was added
  4. temperatureThe reaction was refluxed for forty five minutes
  5. temperaturecooled
  6. filtrationfiltered through Celite under nitrogen
  7. concentrationconcentrated in vacuo
  8. concentrationconcentrated in vacuo
  9. filtrationfiltered through Celite
  10. washThe filtrate washed with water two times, saturated sodium chloride solution
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customThe product was recrystallized (methanol)

Sources & evidence

ORD record
ord-ec745acc8ef74ee1a328678c818da859
Source dataset
uspto-grants-2004_10
Patent number
US06800646B1

Linked notes

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