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

HRID 1067993

反応式

HRID 1067993 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-267e1980de664fa4b42f10e4d4b3a9d2
出典データセット
uspto-grants-2001_06
特許番号
US06248739B1

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