N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamide → N-[6-chloro-2-(3-cyanopropyl)-5-quinolinyl]-cyclohexaneacetamide

HRID 2217867

Reaktionsgleichung

Reaktionsgleichung von HRID 2217867
Br[Zn][CH2:3][CH2:4][CH2:5][C:6]#[N:7].Cl[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:29])[C:15]=2[NH:19][C:20](=[O:28])[CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:10]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[NH4+]>[Cl:29][C:14]1[C:15]([NH:19][C:20](=[O:28])[CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH2:3][CH2:4][CH2:5][C:6]#[N:7])[CH:18]=[CH:17]2

Komponenten

5

Edukt 2

HCID 86012996N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamideHCID 178511035HCID 178511035, Verbindung

Produkt 1

HCID 68809609N-[6-chloro-2-(3-cyanopropyl)-5-quinolinyl]-cyclohexaneacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

Bromo(3-cyanopropyl)-zinc (30 mL, 0.5 M in tetrahydrofuran) and tetrakis(triphenylphosphine)palladium(0) (86 mg) were added to N-(2,6-dichloro-5-quinolinyl)-cyclohexaneacetamide (Example 1(a)) (500 mg). The reaction mixture was heated to reflux for 30 minutes. The mixture was cooled to room temperature and then poured into aqueous saturated ammonium chloride solution (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried, filtered and evaporated. Purification (SiO2, methanol:dichloromethane 3:97 as eluant) gave the sub-title compound as a solid (490 mg).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 minutes
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. customThe combined organic extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customPurification (SiO2, methanol:dichloromethane 3:97 as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-8be4569d1ec84e37980886f9c3832abb
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07408065B2

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