4-Benzyloxy-3-chloroaniline → N-{4-[4-(Benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}acetamide

HRID 1013915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013915
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH2:17][CH3:18])=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:19]#[N:20].[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][C:30]=1[Cl:36])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl.N1C=CC=CC=1>C(O)(C)C>[CH2:21]([O:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:16][CH2:17][CH3:18])=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:19]#[N:20])=[CH:31][C:30]=1[Cl:36])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Komponenten

5

Edukt 3

HCID 12682854-Benzyloxy-3-chloroanilineHCID 10176127Pyridinium chlorideHCID 11358234N-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl)acetamide

Produkt 1

HCID 67315262N-{4-[4-(Benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 4.17 g (0.0149 moles) of the N-(4-chloro-3-cyano-7-ethoxy-6-quinolinyl)acetamide, 4.04 g (0.0173 moles) of 4-benzyloxy-3-chloro-phenylamine (example 5), and 2.0 g (0.017 moles) of pyridine hydrochloride in 85 ml of isopropanol was stirred and refluxed in an oil bath for 30 minutes. The reaction was cooled in an ice bath, and the solid was collected by filtration and washed with isopropanol, and then with ether yielding 7.26 g of crude product as the hydrochloride salt. This material was purified by chromatography of the free base on silica gel by elution with 1:39 methanol-methylene chloride.

Aufarbeitung

  1. temperaturerefluxed in an oil bath for 30 minutes
  2. temperatureThe reaction was cooled in an ice bath
  3. filtrationthe solid was collected by filtration
  4. washwashed with isopropanol
  5. customThis material was purified by chromatography of the free base on silica gel by elution with 1:39 methanol-methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-5bdd1ac5a20648a8b7b8082f77ada418
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07982043B2

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