2,4,6-Trimethylpyridine → N-(4-Chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

HRID 1067993

Reaktionsgleichung

Reaktionsgleichung von HRID 1067993
[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]O)[CH:17]=3)[N:12]([CH3:23])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.N1C(C)=CC(C)=CC=1C.CS([Cl:39])(=O)=O>CN(C1C=CN=CC=1)C.CN(C=O)C>[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:39])[CH:17]=3)[N:12]([CH3:23])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 15516933N-(4-Chlorobenzyl)-6-(hydroxymethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Produkt 1

HCID 21192571N-(4-Chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-(4-chlorobenzyl)-6-(hydroxymethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide from Preparation No. 10 (1.0 g), collidine (0.44 mL), and DMAP (57.9 mg) in anhydrous DMF (48 mL) is cooled to 0° C. Methanesulfonyl chloride (0.24 mL) is added dropwise. The reaction is stirred at room temperature. The crude product is precipitated by addition of water and is filtered. The resulting solid is adsorbed onto silica and purified by chromatography (eluent 100% CH2Cl2 (1 L), 1% MeOH in CH2Cl2 (1 L)). Product-containing fractions were combined and concentrated to afford 948.8 mg (90%) of the title compound as a white solid.

Aufarbeitung

  1. customThe crude product is precipitated by addition of water
  2. filtrationis filtered
  3. custompurified by chromatography (eluent 100% CH2Cl2 (1 L), 1% MeOH in CH2Cl2 (1 L))
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-267e1980de664fa4b42f10e4d4b3a9d2
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248739B1

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