Potassium Carbonate → N-pyrimidinyl piperidine sulfonamide

HRID 392378

反応式

HRID 392378 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 22052662N-pyrimidinyl piperidine sulfonamide収率 68%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-5df86d4fe8ef4b8b871554e8aaa5b568
出典データセット
uspto-grants-2004_10
特許番号
US06800646B1

関連ノート

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