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

HRID 1594867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594867
F[C:2]1[CH:9]=[C:8]([CH2:10][C:11]2[N:12]=[CH:13][N:14]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:35]([C:37]1([C:45]2[CH:50]=[CH:49][CH:48]=[C:47]([OH:51])[CH:46]=2)[CH2:43][CH2:42][CH2:41][CH2:40][NH:39][C:38]1=[O:44])[CH3:36].[F-].[K+].[CH2:54]1OCCOCCOCCOCCOCCOC1>CC#N>[CH2:35]([C:37]1([C:45]2[CH:46]=[C:47]([CH:48]=[CH:49][CH:50]=2)[O:51][C:2]2[CH:9]=[C:8]([CH2:10][C:11]3[N:12]=[CH:13][N:14]([C:16]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:15]=3)[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:43][CH2:42][CH2:41][CH2:40][N:39]([CH3:54])[C:38]1=[O:44])[CH3:36]

Komponenten

6

Edukt 4

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 109612242-Fluoro-4-(1-trityl-1h-imidazol-4-ylmethyl)-benzonitrileHCID 217062193-Ethyl-3-(3-hydroxy-phenyl)-azepan-2-one

Produkt 1

HCID 109085302-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(1-trityl-1H-imidazol-4-ylmethyl)-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Fluoro-4-(1-trityl-1H-imidazol-4-ylmethyl)-benzonitrile (as described in Step A above) (0.348 g, 0.784 mmol), 3-ethyl-3-(3-hydroxy-phenyl)-1-methyl-azepan-2-one (as described in Example 8, Step B) (0.194 mg, 0.784 mmol), KF.Al2O3 (0.232 g) and 18-Crown-6 (0.020 g, 0.076 mmol) were refluxed in CH3CN (15 mL) under Ar for 48 h. The solution was concentrated in vacuo, diluted with EtOAc, washed with 1N NaOH solution, water, brine, dried (MgSO4), concentrated and purified using SiO2 chromatography (1.0% MeOH/CH2Cl2) to give the title compound.

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washwashed with 1N NaOH solution, water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-fb5eee15428846fc8d9d2c838f6c79ab
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06284755B1

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