18-Crown-6 → 2-[3-(3-Ethyl-2-oxo-azepan-3-yl)-phenoxy]-4-imidazol-1-ylmethyl-benzonitrile

HRID 1594858

Reaktionsgleichung

Reaktionsgleichung von HRID 1594858
F[C:2]1[CH:9]=[C:8]([CH2:10][N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:16]([C:18]1([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)[CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:19]1=[O:25])[CH3:17].[F-].[K+].C1OCCOCCOCCOCCOCCOC1>CC#N>[CH2:16]([C:18]1([C:26]2[CH:27]=[C:28]([CH:29]=[CH:30][CH:31]=2)[O:32][C:2]2[CH:9]=[C:8]([CH2:10][N:11]3[CH:15]=[CH:14][N:13]=[CH:12]3)[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:24][CH2:23][CH2:22][CH2:21][NH:20][C:19]1=[O:25])[CH3:17]

Komponenten

6

Edukt 4

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 21697068Benzonitrile, 2-fluoro-4-(1H-imidazol-1-ylmethyl)-HCID 21706219HCID 21706219, Verbindung

Produkt 1

HCID 110370902-[3-(3-Ethyl-2-oxo-azepan-3-yl)-phenoxy]-4-imidazol-1-ylmethyl-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Fluoro-4-imidazol-1-ylmethyl-benzonitrile (as described in Example 1, Step E) (0.065 g, 0.325 mmol), 3-ethyl-3-(3-hydroxy-phenyl)-azepan-2-one (as described in Step B above) (0.076 g, 0.325 mmol), KF.Al2O3 (0.091 g) and 18-Crown-6 (0.008 g, 0.030 mmol) were refluxed in CH3CN (8 mL) under Ar for 72 h. The solution was filtered, concentrated in vacuo, and purified using SiO2 chromatography (0.5-3.0% MeOH/CH2Cl2). The compound was treated with 1N HCl ethereal solution to give the title compound.

Aufarbeitung

  1. filtrationThe solution was filtered
  2. concentrationconcentrated in vacuo
  3. custompurified
  4. additionThe compound was treated with 1N HCl ethereal solution

Quellen und Nachweise

ORD-Eintrag
ord-9098ffd1b25046b9878da1ffb307ece8
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06284755B1

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