Diisopropylethylamine → (E)-4-Ethyl-1-[4-[2-methyl-7-(trifluoromethyl)-4-quinolyl]piperazin-1-yl]hex-2-en-1-one

HRID 333959

Reaktionsgleichung

Reaktionsgleichung von HRID 333959
[CH2:1]([CH:3]([CH2:9][CH3:10])/[CH:4]=[CH:5]/[C:6]([OH:8])=O)[CH3:2].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:44][C:45]1[CH:54]=[C:53]([N:55]2[CH2:60][CH2:59][NH:58][CH2:57][CH2:56]2)[C:52]2[C:47](=[CH:48][C:49]([C:61]([F:64])([F:63])[F:62])=[CH:50][CH:51]=2)[N:46]=1>CN(C=O)C>[CH2:9]([CH:3]([CH2:1][CH3:2])/[CH:4]=[CH:5]/[C:6]([N:58]1[CH2:59][CH2:60][N:55]([C:53]2[C:52]3[C:47](=[CH:48][C:49]([C:61]([F:64])([F:62])[F:63])=[CH:50][CH:51]=3)[N:46]=[C:45]([CH3:44])[CH:54]=2)[CH2:56][CH2:57]1)=[O:8])[CH3:10]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 6437410(E)-4-Ethylhex-2-enoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668357982-Methyl-4-piperazin-1-yl-7-(trifluoromethyl)quinoline

Produkt 1

HCID 56949204(E)-4-Ethyl-1-[4-[2-methyl-7-(trifluoromethyl)-4-quinolyl]piperazin-1-yl]hex-2-en-1-oneAusbeute 320 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(E)-4-Ethyl-hex-2-enoic acid (21.3 mg, 0.15 mmol) was dissolved in DMF (350 μl), diisopropylethylamine was added (26 μl, 0.15 mmol) followed by HATU (57 mg, 0.15 mmol dissolved in 0.25 ml DMF). The mixture was stirred at room temperature for 15 minutes, then 2-methyl-4-piperazin-1-yl-7-(trifluoromethyl)quinoline (44 mg, 0.15 mmol, dissolved in 1 ml DMF) was added and stirring was continued overnight. The mixture was evaporated under reduced pressure, the residue was dissolved in dichloromethane, the solution was washed with 5% sodium bicarbonate solution and water, evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 20.3 mg (0.48 mmol, 32.3%) of a solid.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued overnight
  3. customThe mixture was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washthe solution was washed with 5% sodium bicarbonate solution and water
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)

Quellen und Nachweise

ORD-Eintrag
ord-23d9052b54ca46bc91e6c5c92c1738e0
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883791B2

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