Hydrochloric Acid → 8-(3-(1-(4-Chlorophenyl)-2-(pyridin-4-yl)ethyl)phenyl)-6-isopropylquinoline

HRID 896684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896684
C(OC(=O)[CH:5]([C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1)[CH:6]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[C:15]([CH:23]([CH3:25])[CH3:24])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[CH:8]=1)C.[OH-].[Na+].Cl>C1COCC1.CCO.C(OCC)(=O)C>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH:6]([C:7]2[CH:8]=[C:9]([C:13]3[CH:14]=[C:15]([CH:23]([CH3:25])[CH3:24])[CH:16]=[C:17]4[C:22]=3[N:21]=[CH:20][CH:19]=[CH:18]4)[CH:10]=[CH:11][CH:12]=2)[CH2:5][C:33]2[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=2)=[CH:27][CH:28]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 208149663-(4-Chloro-phenyl)-3-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-2-pyridin-4-yl-propionic acid ethyl ester

Produkt 1

HCID 101831968-(3-(1-(4-Chlorophenyl)-2-(pyridin-4-yl)ethyl)phenyl)-6-isopropylquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 21873804Tetrahydrofuran ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of the crude ester from Step 3 above in THF/EtOH (10 mL) was added NaOH (2N, 2 mL). The resulting reaction mixture was stirred 18 h at 100° C. then neutralized with HCl 6N to pH 7 and diluted with ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 1:1) provided the 8-{3-[1-(4-chloro-phenyl)-2-pyridin-4-yl-ethyl]-phenyl}-6-isopropyl-quinoline compound.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. washby flash chromatography (eluting with hexane/ethyl acetate, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-18cb4c5d5fee4d0991dae9e76022921f
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919353B2

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