Dimethylformamide → N-picolyl piperidine sulfonamide

HRID 842244노트

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HRID 842244 반응식
N1C=CC=CC=1CN1CCC([S:18]([N:21]2[CH2:26][CH2:25][CH:24](OC3C=CC(OC(F)(F)F)=CC=3)[CH2:23][CH2:22]2)(=[O:20])=[O:19])(C(OC)=O)CC1.C(=O)([O-])[O-].[K+].[K+].Cl.[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH2:52]Cl.C[N:55](C)C=O>>[N:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[CH2:52][NH:55][S:18]([N:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)(=[O:19])=[O:20]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 22052615Methyl 1-(2-pyridinylmethyl)-4-[[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]sulfonyl]-4-piperidinecarboxylate

생성물 1

HCID 30666388N-picolyl piperidine sulfonamide수율 72%

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온도
35 °C

실험 절차

Part I: Preparation of methyl 1-(2-pyridinylmethyl)-4-[[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]sulfonyl]-4-piperidinecarboxylate. The unsubstituted piperidine sulfonamide from part H (7.9 g, 16.95 mmol) was dissolved in dry dimethylformamide (35 mL) and potassium carbonate (7.05 g, 51.1 mmol) and 2-picolyl chloride hydrochloride (4.21 g, 25.67 mmol) were added. The reaction was stirred at 35° C. for sixteen 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. Chromatography (on silica, ethyl acetate/hexanes) provided the N-picolyl piperidine sulfonamide as a white solid (6.8 g, 72%).

후처리

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered through Celite
  3. washThe filtrate washed with water two times, saturated sodium chloride solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-ce267b546c104d41880163c34c3b0832
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06372758B1

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