Diisopropylethylamine → HCID 57444322, Verbindung

HRID 15833

Reaktionsgleichung

Reaktionsgleichung von HRID 15833
C(N(CC)C(C)C)(C)C.[CH3:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[C:14]([F:27])[CH:15]=[CH:16][C:17]=2[N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[N:12]=1.CS(O[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-:43])=[O:42])[CH:36]=1)(=O)=O>CN(C)C=O>[F:27][C:14]1[CH:15]=[CH:16][C:17]([N:21]2[CH2:26][CH2:25][N:24]([CH2:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-:43])=[O:42])[CH:36]=3)[CH2:23][CH2:22]2)=[C:18]2[C:13]=1[N:12]=[C:11]([CH3:10])[CH:20]=[CH:19]2

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 219738843-Nitrophenethyl methanesulfonateHCID 574443218-Fluoro-2-methyl-5-piperazin-1-yl-quinoline

Produkt 1

HCID 57444322HCID 57444322, VerbindungAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

N,N-Diisopropylethylamine (0.25 mL; 3 eq) was added to a solution of 2-methyl-5-(1-piperazinyl)-8-fluoro quinoline (0.170 g; 1 eq) and 2-(3-nitrophenyl)ethyl methanesulfonate (D4) (0.17 g; 1 eq) in dimethylformamide (4.0 mL). The reaction mixture was heated to 100° C. for 10 hours. The dark solution was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with water (3 mL) and brine (1 mL) and extracted into ethyl acetate (3×3 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The crude was purified by flash chromatography on silica gel, eluting with a gradient from dichloromethane to dichloromethane-methanol (98:2) affording the title compound in 46% yield (0.126 g).

Aufarbeitung

  1. temperatureThe dark solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water (3 mL) and brine (1 mL)
  4. extractionextracted into ethyl acetate (3×3 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by flash chromatography on silica gel
  8. washeluting with a gradient from dichloromethane to dichloromethane-methanol (98:2)

Quellen und Nachweise

ORD-Eintrag
ord-9125748467914a7fb21ad5afe123e231
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732600B2

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