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 323498

Reaktionsgleichung

Reaktionsgleichung von HRID 323498
[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]

Komponenten

6

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2e0e76fe92c548f4a59f5418cc16215f
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211199B1

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