Triethylamine → 1-(3,4,5-trimethoxybenzyl)-3-(3-(4-(1-(ethoxycarbonylmethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)propyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine

HRID 323498노트

반응식

HRID 323498 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)([CH2:12][CH2:13][CH2:14]OS(C)(=O)=O)[C:8]1=[O:28].I.[CH2:37]([O:39][C:40]([CH2:42][N:43]1[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=2[N:45]=[C:44]1[NH:52][CH:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1)=[O:41])[CH3:38].C(N(CC)CC)C>C(#N)C.ClCCl>[CH3:35][O:34][C:30]1[CH:29]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:31]=1[O:32][CH3:33])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:12][CH2:13][CH2:14][N:56]2[CH2:57][CH2:58][CH:53]([NH:52][C:44]3[N:43]([CH2:42][C:40]([O:39][CH2:37][CH3:38])=[O:41])[C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][C:46]=4[N:45]=3)[CH2:54][CH2:55]2)([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C:8]1=[O:28]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 184644831-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-methanesulfonyloxypropyl)-2-oxopyrrolidineHCID 86756599(1-(ethoxycarbonylmethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine hydriodic acid salt

생성물 1

HCID 99618421-(3,4,5-trimethoxybenzyl)-3-(3-(4-(1-(ethoxycarbonylmethyl)-1H-benzimidazol-2-yl-amino)piperidin-1-yl)propyl)-3-(4-fluorophenylmethyl)-2-oxopyrrolidine

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

Combine 1-(3,4,5-trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-methanesulfonyloxypropyl)-2-oxopyrrolidine (0.35 g, 0.68 mmol), (1-(ethoxycarbonylmethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine hydriodic acid salt (0.38 g, 0.68 mmol), and triethylamine (0.276 g, 2.72 mmol) in acetonitrile (15 mL). Heat to reflux. After 12 hours, cool the reaction mixture, dilute with dichloromethane, and extract with brine. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 5% methanol/0.5% concentrate aqueous ammonium hydroxide/dichloromethane to give the title compound.

후처리

  1. temperatureHeat to reflux
  2. temperaturecool the reaction mixture
  3. extractionextract with brine
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto obtain a residue
  8. concentrationChromatograph the residue on silica gel eluting with 5% methanol/0.5% concentrate aqueous ammonium hydroxide/dichloromethane

출처 및 근거

ORD 기록
ord-2e0e76fe92c548f4a59f5418cc16215f
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

반응 노트

불러오는 중…