Water → 6-(azidomethyl)-N-[(4-chlorophenyl)methyl]-1-methyl-4-oxo-quinoline-3-carboxamide

HRID 1067994

Reaktionsgleichung

Reaktionsgleichung von HRID 1067994
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21]Cl)[CH:17]=3)[N:12]([CH3:23])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[N-:26]=[N+:27]=[N-:28].[Na+].O>CN(C=O)C>[N:26]([CH2:21][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:23])[CH:11]=[C:10]([C:8]([NH:7][CH2:6][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:25][CH:24]=1)=[O:9])[C:19]2=[O:20])=[N+:27]=[N-:28]

Komponenten

5

Edukt 3

HCID 962WaterHCID 33557Sodium AzideHCID 21192571N-(4-Chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Produkt 1

HCID 160738676-(azidomethyl)-N-[(4-chlorophenyl)methyl]-1-methyl-4-oxo-quinoline-3-carboxamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-(4-chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide from Preparation No. 35 (200 mg) and sodium azide (176.8 mg) in anhydrous DMF (7 mL) is heated at 60° C. overnight. The reaction is cooled to room temperature and poured into water to precipitate the product. The solid is adsorbed onto silica and purified by chromatography (eluent 100% CH2Cl2 (1 L), 0.5% MeOH in CH2Cl2 (1 L), and 1% MeOH in CH2Cl2 (1 L)). Fractions homogenous by TLC were combined and concentrated to afford 182.7 mg (90%) of the title compound as a white solid.

Aufarbeitung

  1. customto precipitate the product
  2. custompurified by chromatography (eluent 100% CH2Cl2 (1 L), 0.5% MeOH in CH2Cl2 (1 L), and 1% MeOH in CH2Cl2 (1 L))
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f28d5da9822f4be49a14b3bc9792e760
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248739B1

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