Potassium Carbonate → [1-[2-[3-(3,4-Dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]-[1-(pyridin-2-ylmethyl)benzimidazol-2-yl]methanone

HRID 2269860노트

반응식

HRID 2269860 반응식
CS(O)(=O)=[O:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:45]=[C:46]([O:50][CH3:51])[C:47]=1[O:48][CH3:49])[C:11]([N:13]1[CH2:17][CH2:16][C:15]([CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][CH:31]([C:34]([C:36]3[NH:40][C:39]4[CH:41]=[CH:42][CH:43]=[CH:44][C:38]=4[N:37]=3)=[O:35])[CH2:30][CH2:29]2)([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH2:14]1)=[O:12].Cl.[Cl:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][N:56]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[Cl:53][CH2:20][Cl:25].[CH3:6][OH:7].[OH-:3].[NH4+:13].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:45]=[C:46]([O:50][CH3:51])[C:47]=1[O:48][CH3:49])[C:11]([N:13]1[CH2:17][CH2:16][C:15]([CH2:26][CH2:27][N:28]2[CH2:29][CH2:30][CH:31]([C:34]([C:36]3[N:37]([CH2:54][C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][N:56]=4)[C:38]4[CH:44]=[CH:43][CH:42]=[CH:41][C:39]=4[N:40]=3)=[O:35])[CH2:32][CH2:33]2)([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH2:14]1)=[O:12]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 867576761-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1 H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-(3,4-dichloro-phenyl)-pyrrolidine methanesulfonate salt

생성물 2

HCID 10147107[1-[2-[3-(3,4-Dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]-[1-(pyridin-2-ylmethyl)benzimidazol-2-yl]methanoneHCID 21896990Dichloromethane methanol ammonium hydroxide

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1 H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-(3,4-dichloro-phenyl)-pyrrolidine methanesulfonate salt (0.60 g, 0.70 mmol) and 2-(chloromethyl)pyridine hydrochloride (0.46 g, 2.8 mmol), and potassium carbonate (1.14 g, 8.25 mmol) in acetone (12 mL) and water (4 mL). Heat to reflux. After 24 hours, cool to ambient temperature and concentrate the reaction mixture in vacuo and dilute with ethyl acetate. Extract with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 10/1/0.1 dichloromethane/methanol/ammonium hydroxide to give the title compound: Rf=0.58 (silica gel, 10/1/0.1 dichloromethane/methanol/ammonium hydroxide).

후처리

  1. temperatureHeat to reflux
  2. concentrationconcentrate the reaction mixture in vacuo
  3. additiondilute with ethyl acetate
  4. extractionExtract with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customto give a residue

출처 및 근거

ORD 기록
ord-464f05cb9c6548b8a11ca1676dc801f2
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06329392B1

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