Potassium Carbonate → N-pyrimidinyl piperidine sulfonamide

HRID 842246ノート

反応式

HRID 842246 の反応式
FC(F)(F)C1C=CC(OC2CCN(S(C3(C(OC)=O)CCN([C:23]4[N:28]=[C:27](C(F)(F)F)[CH:26]=[CH:25][N:24]=4)CC3)(=O)=O)CC2)=CC=1.[N:41]1([S:47]([NH2:50])(=[O:49])=[O:48])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1.C([O-])=O.[NH4+].C(=O)([O-])[O-].[K+].[K+].ClC1N=C(C(F)(F)F)C=CN=1>CO.CN(C)C=O>[N:24]1[CH:25]=[CH:26][CH:27]=[N:28][C:23]=1[NH:50][S:47]([N:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)(=[O:49])=[O:48]

参加物

8

反応物 5

HCID 11430Potassium CarbonateHCID 2767411-PiperidinesulfonamideHCID 2723923Ammonium formateHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidineHCID 22052660Methyl 4-[[4-[4-(trifluoromethyl)phenoxy]-1-piperidinyl]-sulfonyl]-1-[4-(trifluoromethyl)-2-pyrimidinyl]-4-piperidinecarboxylate

生成物 1

HCID 22052662N-pyrimidinyl piperidine sulfonamide収率 76%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

Part G: Preparation of methyl 4-[[4-[4-(trifluoromethyl)phenoxy]-1-piperidinyl]-sulfonyl]-1-[4-(trifluoromethyl)-2-pyrimidinyl]-4-piperidinecarboxylate. 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 min. 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 min, cooled, filtered through Celite under N2, 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 70° C. for 3 hr, 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%).

後処理

  1. customThe system was purged with nitrogen for 10 min
  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 min
  5. temperaturecooled
  6. filtrationfiltered through Celite under N2
  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-4a98f606c7864cf7943e8daff44f382f
出典データセット
uspto-grants-2002_04
特許番号
US06372758B1

反応ノート

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