Ethyl Methanesulfonate → 4-[(5-Chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-1-ethyl-3-pyrrolidinyl]-oxy}phenyl)-1H-pyridin-2-one

HRID 15081

반응식

HRID 15081 반응식
CS(OCC)(=O)=O.C(#N)C.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][N:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C@@H:33]4[CH2:37][CH2:36][N:35]([CH:38](C)[CH3:39])[CH2:34]4)=[CH:28][CH:27]=3)[C:22](=[O:41])[CH:21]=2)=[N:16][CH:17]=1>C(Cl)(Cl)Cl>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][N:23]([C:26]3[CH:27]=[CH:28][C:29]([O:32][C@@H:33]4[CH2:37][CH2:36][N:35]([CH2:38][CH3:39])[CH2:34]4)=[CH:30][CH:31]=3)[C:22](=[O:41])[CH:21]=2)=[N:16][CH:17]=1

참가 물질

5

반응물 3

HCID 6113Ethyl Methanesulfonate2회HCID 6342AcetonitrileHCID 116119264-[(5-Chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-1-isopropyl-3-pyrrolidinyl]-oxy}phenyl)-1H-pyridin-2-one

생성물 1

HCID 115319734-[(5-Chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-1-ethyl-3-pyrrolidinyl]-oxy}phenyl)-1H-pyridin-2-one수율 41.3%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
80 °C

실험 절차

Ethyl methanesulfonate (0.45 mL) was added to acetonitrile solution of 4-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{[(3R)-3-pyrrolidinyl]oxy}phenyl)-1H-pyridin-2-one (1.65 g, Example 122), and stirred at 80° C. for 2 hours. Additional ethyl methanesulfonate (0.45 mL) was added and stirred at 80° C. for further 2 hours, followed by cooling to room temperature. Chloroform was added to the reaction liquid which then was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous potassium carbonate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:100-1:10-1:4). The residue was crystallized from mixed solvent of ethyl acetate and heptane to provide the title compound (660 mg).

후처리

  1. stirringstirred at 80° C. for further 2 hours
  2. temperatureby cooling to room temperature
  3. washthen was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  4. dry with materialdried over anhydrous potassium carbonate
  5. concentrationConcentrating the solvent under reduced pressure
  6. customthe residue was purified on silica gel column chromatography (C-300; methanol:chloroform=1:100-1:10-1:4)
  7. customThe residue was crystallized
  8. additionfrom mixed solvent of ethyl acetate and heptane

출처 및 근거

ORD 기록
ord-01d3e5beed11407cab04b5788599f5fc
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732456B2

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