Water → (+/-)-4-(3-chlorophenyl)-6-[hydroxy[4-(1-hydroxyethyl)phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone

HRID 346997Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 346997
[Li][CH3:2].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:35])([C:29]4[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=4)[C:21]4[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=4)[CH:18]=3)[N:13]([CH3:36])[C:12](=[O:37])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1.O>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:35])([C:21]4[CH:28]=[CH:27][C:24]([CH:25]([OH:26])[CH3:2])=[CH:23][CH:22]=4)[C:29]4[N:33]([CH3:34])[CH:32]=[N:31][CH:30]=4)[CH:18]=3)[N:13]([CH3:36])[C:12](=[O:37])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 10299684(+/-)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzaldehydeHCID 178418348HCID 178418348, Verbindung

Produkt 1

HCID 21082093(+/-)-4-(3-chlorophenyl)-6-[hydroxy[4-(1-hydroxyethyl)phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinoneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

MeLi (0.00258 mol) was added dropwise at −70° C. to a solution of (±)-4-[[4-(3-chlorophenyl)-1,2-dihydro-1-methyl-2-oxo-6-quinolinyl]hydroxy(1-methyl-1H-imidazol-5yl)methyl]benzaldehyde (described in Example B6) (0.001 mol) in THF (5 ml) under N2 flow. The mixture was stirred at −70° C. for 2 hours. H2O was added. The mixture was extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (0.9 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 95/5/0.2; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 0.3 g (58%) of (±)-4-(3-chlorophenyl)-6-[hydroxy[4-(1-hydroxyethyl)phenyl](1-methyl-1H-imidazol-5-yl)methyl]-1-methyl-2(1H)-quinolinone, mp. 181° C.

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue (0.9 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH; 95/5/0.2; 15–40 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-04c2a36c8e6a4373a9df77bfa3cf54d0
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173040B2

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