Potassium Carbonate → N-pyrimidinyl piperidine sulfonamide

HRID 392378

Reaktionsgleichung

Reaktionsgleichung von HRID 392378
[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]=[CH:26][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]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 2767411-PiperidinesulfonamideHCID 2723923Ammonium formate

Produkt 1

HCID 22052662N-pyrimidinyl piperidine sulfonamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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 (6.21 g, 13.8 mmol) was dissolved in dry dimethylformamide (28 mL) and potassium carbonate (5.7 g, 41.4 mmol) and 2-chloropyrimidine (3.16 g, 27.6 mmol) were added. The reaction was stirred at eighty five degrees Celsius for one 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 (4.94 g, 68%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-5df86d4fe8ef4b8b871554e8aaa5b568
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800646B1

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