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 2269860ノート

反応式

HRID 2269860 の反応式
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]

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-464f05cb9c6548b8a11ca1676dc801f2
出典データセット
uspto-grants-2001_12
特許番号
US06329392B1

反応ノート

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