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Potassium Carbonate → 4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-1-ethoxycarbonylmethyl-2-ethyl-1H-benzimidazole

HRID 2287571
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2287571
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([OH:16])[C:10]=2[N:9]=[C:8]1[CH2:17][CH3:18])=[O:5])[CH3:2].[Cl:19][C:20]1[C:27]([N:28]([CH3:47])[C:29](=[O:46])[CH2:30][NH:31][C:32](=[O:45])[CH:33]=[CH:34][C:35]2[CH:40]=[CH:39][C:38]([C:41](=[O:44])[NH:42][CH3:43])=[CH:37][CH:36]=2)=[CH:26][CH:25]=[C:24]([Cl:48])[C:21]=1[CH2:22]Br.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:19][C:20]1[C:27]([N:28]([CH3:47])[C:29](=[O:46])[CH2:30][NH:31][C:32](=[O:45])[CH:33]=[CH:34][C:35]2[CH:36]=[CH:37][C:38]([C:41](=[O:44])[NH:42][CH3:43])=[CH:39][CH:40]=2)=[CH:26][CH:25]=[C:24]([Cl:48])[C:21]=1[CH2:22][O:16][C:15]1[C:10]2[N:9]=[C:8]([CH2:17][CH3:18])[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:11]=2[CH:12]=[CH:13][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 212546631-ethoxycarbonylmethyl-2-ethyl-4-hydroxy-1H-benzimidazoleHCID 538052362,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyl bromide

Produkt 1

HCID 53670718
4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-1-ethoxycarbonylmethyl-2-ethyl-1H-benzimidazole
Ausbeute 82,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-ethoxycarbonylmethyl-2-ethyl-4-hydroxy-1H-benzimidazole (140 mg) and 2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyl bromide (289 mg) in dimethylformamide (3 ml) was added potassium carbonate (117 mg) under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature and then for 2 hours at ambient temperature. To the reaction mixture was added saturated sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel flash chromatography (5% methanol-ethyl acetate) and pulverized with diisopropyl ether to give 4-[2,6-dichloro-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzyloxy]-1-ethoxycarbonylmethyl-2-ethyl-1H-benzimidazole (317 mg) as pale yellow solid.

Aufarbeitung

  1. temperaturecooling
  2. waitfor 2 hours at ambient temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel flash chromatography (5% methanol-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-58c83f0a948f4d0483f185b623f5d781
Quelldatensatz
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06083961

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