Sodium Iodide → N-{2-[ethyl(2-hydroxyethyl)amino]ethyl}-3-methoxy-N-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]quinoline-2-carboxamide

HRID 1947131

Reaktionsgleichung

Reaktionsgleichung von HRID 1947131
Cl[CH2:2][CH2:3][N:4]([CH3:32])[C:5]([C:7]1[S:19][C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]([CH2:20][C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:10](=[O:29])[C:9]=2[C:8]=1[O:30][CH3:31])=[O:6].C(NC([OH:38])C)C.[CH:39]([N:42](C(C)C)[CH2:43][CH3:44])(C)[CH3:40].[I-].[Na+]>C(O)CCC.C(=O)([O-])O.[Na+]>[CH2:39]([N:42]([CH2:43][CH2:44][OH:38])[CH2:2][CH2:3][N:4]([CH3:32])[C:5]([C:7]1[S:19][C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]([CH2:20][C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:10](=[O:29])[C:9]=2[C:8]=1[O:30][CH3:31])=[O:6])[CH3:40]

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 18179409EthylaminoethanolHCID 66893214N-(2-chloroethyl)-3-methoxy-N-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]quinoline-2-carboxamide

Produkt 1

HCID 57860044N-{2-[ethyl(2-hydroxyethyl)amino]ethyl}-3-methoxy-N-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]quinoline-2-carboxamideAusbeute 35,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of the obtained N-(2-chloroethyl)-3-methoxy-N-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]quinoline-2-carboxamide (200 mg, 0.43 mmol), N-ethylaminoethanol (228 mg, 2.55 mmol), diisopropylethylamine (330 mg, 2.55 mmol) and sodium iodide (64 mg, 0.43 mmol) in 1-butanol (5 mL) was stirred at 110° C. for 18 hr. The reaction mixture was diluted with saturated sodium hydrogen carbonate solution, and extracted twice with ethyl acetate. The extract was combined, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by aminosilica gel chromatography (eluate; ethyl acetate to ethyl acetate/methanol=20/1) to give N-{2-[ethyl(2-hydroxyethyl)amino]ethyl}-3-methoxy-N-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-4,5-dihydrothieno[3,2-c]quinoline-2-carboxamide (0.08 g) as a white non-crystalline solid.

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by aminosilica gel chromatography (eluate; ethyl acetate to ethyl acetate/methanol=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-d0b7c70b85434e81a27e4d0ccaf93e95
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399449B2

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