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Pyridine → 5-{4-[6-(4-Acetylamino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl}thiazolidine-2,4-dione hydrochloride

HRID 2303763
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2303763
[ClH:1].Cl.[NH2:3][C:4]1[C:36]([CH3:37])=[CH:35][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:32]=[CH:31][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:21][CH:20]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:6][C:5]=1[CH3:38].[C:39](OC(=O)C)(=[O:41])[CH3:40].N1C=CC=CC=1>CN(C1C=CN=CC=1)C.O1CCCC1>[ClH:1].[C:39]([NH:3][C:4]1[C:5]([CH3:38])=[CH:6][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[N:16]=[C:15]([CH2:17][O:18][C:19]4[CH:20]=[CH:21][C:22]([CH2:23][CH:24]5[S:28][C:27](=[O:29])[NH:26][C:25]5=[O:30])=[CH:31][CH:32]=4)[N:14]([CH3:33])[C:13]=3[CH:34]=2)=[CH:35][C:36]=1[CH3:37])(=[O:41])[CH3:40]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 16719220Efatutazone Dihydrochloride

Produkt 1

HCID 867584265-{4-[6-(4-Acetylamino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl}thiazolidine-2,4-dione hydrochlorideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 155 mg of 5-{4-[6-(4-amino-3,5-dimethylphenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl}thiazolidine-2,4-dione dihydrochloride, 36 mg of acetic anhydride, 107 mg of pyridine, 7.3 mg of 4-(N,N-dimethylamino)pyridine and 5 ml of anhydrous tetrahydrofuran was heated under reflux for 2 hours. The reaction mixture was concentrated by evaporation. Water was added to the concentrate, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. To the residue, 10 ml of 4N hydrochloric acid/ethyl acetate were added, followed by stirring at room temperature for 21 hours. The insoluble product was collected by filtration, followed by washing with ether, whereby 97 mg of the title compound were obtained.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated by evaporation
  4. additionWater was added to the concentrate
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionTo the residue, 10 ml of 4N hydrochloric acid/ethyl acetate were added
  9. filtrationThe insoluble product was collected by filtration
  10. washby washing with ether

Quellen und Nachweise

ORD-Eintrag
ord-1461dec41dbf4128bbfe4768b288290d
Quelldatensatz
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06432993B1

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