Diisopropylethylamine → 6-Fluoro-2-methyl-5-{4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinoline

HRID 15830

Reaktionsgleichung

Reaktionsgleichung von HRID 15830
C(N(CC)C(C)C)(C)C.[CH3:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:27])[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:16]1[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](=[CH:14][CH:15]=1)[N:12]=[C:11]([CH3:10])[CH:20]=[CH:19]2

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 219738843-Nitrophenethyl methanesulfonateHCID 574443146-Fluoro-2-methyl-5-(1-piperazinyl)quinoline

Produkt 1

HCID 574443156-Fluoro-2-methyl-5-{4-[2-(3-nitrophenyl)ethyl]-1-piperazinyl}quinolineAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

N,N-Diisopropylethylamine (0.15 mL; 3 eq) was added to a solution of 2-methyl-5-(1-piperazinyl)-6-fluoro quinoline (0.075 g; 1 eq) and 2-(3-nitrophenyl)ethyl methanesulfonate (D4) (0.08; 1.1 eq) in dimethylformamide (3.0 mL). The reaction mixture was heated to 100° C. for 10 hours. The dark solution was concentrated under reduced pressure, diluted with water (3 mL) and brine (1 mL) and extracted into ethyl acetate (3×3 mL). The organic layers were combined, 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 42% yield (0.05 g).

Aufarbeitung

  1. concentrationThe dark solution was concentrated under reduced pressure
  2. additiondiluted with water (3 mL) and brine (1 mL)
  3. extractionextracted into ethyl acetate (3×3 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified by flash chromatography on silica gel
  7. washeluting with a gradient from dichloromethane to dichloromethane-methanol (98:2)

Quellen und Nachweise

ORD-Eintrag
ord-30f07229357c4826a8fbaf23a435d7b8
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732600B2

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