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HCID 43446585, Verbindung → N-(1-(2-(dimethylamino)ethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide

HRID 1922342
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1922342
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])[C:7](=[O:17])[CH2:6][CH2:5]2.I.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](SC)=[NH:25]>C(O)C.CCOCC>[CH3:16][N:14]([CH3:15])[CH2:13][CH2:12][N:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:24]([C:20]3[S:19][CH:23]=[CH:22][CH:21]=3)=[NH:25])=[CH:11][CH:10]=2)[CH2:5][CH2:6][C:7]1=[O:17]
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Komponenten

5

Edukt 2

HCID 43446585HCID 43446585, VerbindungHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Produkt 1

HCID 178483722N-(1-(2-(dimethylamino)ethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)thiophene-2-carboximidamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 6-amino-1-(2-(dimethylamino)ethyl)-3,4-dihydroquinolin-2(1H)-one (0.280 g, 1.20 mmol) in absolute ethanol (5 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.684 g, 2.40 mmol) at room temperature and the resulting mixture was stirred overnight (18 h). The reaction was diluted with ether (45 mL) and the precipitate collected by vacuum filtration. The precipitate was washed from the filter with methanol and the solvent was evaporated. The residue was diluted with 1N sodium hydroxide solution (5 mL) and product was extracted into ethyl acetate (3×10 ml). The combined ethyl acetate layer was washed with brine and dried (Na2SO4). Solvent was evaporated and crude was purified by column chromatography (2M ammonia in methanol:dichloromethane, 1:19). Product was dried under high vacuum. Yield: 230 mg of yellow oil 3 (56%).

Aufarbeitung

  1. filtrationthe precipitate collected by vacuum filtration
  2. washThe precipitate was washed from the
  3. filtrationfilter with methanol
  4. customthe solvent was evaporated
  5. additionThe residue was diluted with 1N sodium hydroxide solution (5 mL) and product
  6. extractionwas extracted into ethyl acetate (3×10 ml)
  7. washThe combined ethyl acetate layer was washed with brine
  8. dry with materialdried (Na2SO4)
  9. customSolvent was evaporated
  10. customcrude was purified by column chromatography (2M ammonia in methanol:dichloromethane, 1:19)
  11. customProduct was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4f3ee861a570485b8cfa63c18a6e5e56
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08173813B2

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