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Water → (E)-1-[3-fluoro-4-(morpholin-4-yl)benzyl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one

HRID 1446530
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1446530
CN(C=O)C.[F:6][C:7]1[CH:8]=[C:9]([CH:34]=[CH:35][C:36]=1[N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)[CH2:10][NH:11][C:12](=[O:33])/[C:13](=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]2)=[C:21]([O:31][CH3:32])[CH:20]=1)/[CH2:14][CH2:15][CH2:16]Cl.[H-].[Na+].O>C(OCC)(=O)C>[F:6][C:7]1[CH:8]=[C:9]([CH:34]=[CH:35][C:36]=1[N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)[CH2:10][N:11]1[CH2:16][CH2:15][CH2:14]/[C:13](=[CH:18]\[C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]3)=[C:21]([O:31][CH3:32])[CH:20]=2)/[C:12]1=[O:33]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 66961400(e)-5-Chloro-2-[3-methoxy-4-(4-methyl-1h-imidazol-1-yl)benzylidene]valeric acid[3-fluoro-4-(morpholin-4-yl)benzyl]amide

Produkt 1

HCID 59170899(E)-1-[3-fluoro-4-(morpholin-4-yl)benzyl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]piperidin-2-one
Ausbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a DMF (4 mL) solution of (E)-5-chloro-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl]benzylidene)valeric acid [3-fluoro-4-(morpholin-4-yl)benzyl]amide (135 mg), sodium hydride was added at 0° C. (40% mineral oil content, 35.6 mg) was added, and the reaction solution was allowed to be warmed to room temperature and agitated for 45 minutes. The reaction solution was cooled to 0° C. after confirming disappearance of the starting materials, water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After washed with a saturated saline solution the organic layer, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. 113 mg of the title compound was obtained by purifying the obtained residue by silica gel chromatography (elution solvent; ethyl acetate→ethyl acetate:ethanol 90:10). The physical properties of the compound are as follows.

Aufarbeitung

  1. additionwas added
  2. temperatureThe reaction solution was cooled to 0° C.
  3. additionwere added to the reaction solution
  4. customthe organic layer was partitioned
  5. washAfter washed with a saturated saline solution the organic layer, it
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1d57a83c05d04c8889e3ac6f7d36179b
Quelldatensatz
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07667041B2

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