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Dimethylformamide → 8-[2,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline

HRID 850180
ノート
印刷プレビュー

反応式

HRID 850180 の反応式
[H-].[Na+].CN(C)C=O.[OH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.[Cl:28][C:29]1[C:36]([N:37]([C:39](=[O:56])[CH2:40][NH:41][C:42](=[O:55])[CH:43]=[CH:44][C:45]2[CH:50]=[CH:49][C:48]([C:51](=[O:54])[NH:52][CH3:53])=[CH:47][CH:46]=2)[CH3:38])=[CH:35][CH:34]=[C:33]([Cl:57])[C:30]=1[CH2:31]Br>O>[Cl:28][C:29]1[C:36]([N:37]([C:39](=[O:56])[CH2:40][NH:41][C:42](=[O:55])[CH:43]=[CH:44][C:45]2[CH:46]=[CH:47][C:48]([C:51](=[O:54])[NH:52][CH3:53])=[CH:49][CH:50]=2)[CH3:38])=[CH:35][CH:34]=[C:33]([Cl:57])[C:30]=1[CH2:31][O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 110867028-Hydroxy-2-methyl-4-(2-pyridylmethoxy)quinolineHCID 538052362,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyl bromide

生成物 1

HCID 545056398-[2,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline
収率 55.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To an ice-cooled mixture of sodium hydride (40% in oil, 9 mg) and anhydrous N,N-dimethylformamide (1 ml) was added 8-hydroxy-2-methyl-4-(2-pyridylmethoxy)quinoline (53 mg), and the mixture was stirred at the same temperature for 30 minutes. To this mixture was added 2,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyl bromide (103 mg), and the mixture was stirred at ambient temperature for 2.5 hours. Water (2 ml) was slowly added to the reaction mixture under ice-water cooling and the precipitates were collected by vacuum filtration and washed with water and diethyl ether. The crude product was purified by a preparative thin layer chromatography (chloroform-methanol-ammonium hydroxide) followed by trituration with ethyl acetate to give 8-[2,6-dichloro-3-[N-[4-(methylcarbamoyl)cinnamoylglycyl]-N-methylamino]benzyloxy]-2-methyl-4-(2-pyridylmethoxy)quinoline (77 mg) as a pinkish powder.

後処理

  1. stirringthe mixture was stirred at ambient temperature for 2.5 hours
  2. filtrationthe precipitates were collected by vacuum filtration
  3. washwashed with water and diethyl ether
  4. customThe crude product was purified by a preparative thin layer chromatography (chloroform-methanol-ammonium hydroxide)

出典と根拠

ORDレコード
ord-60f80bf24d2740bbb1607c62447a3a50
出典データセット
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06015818

反応ノート

読み込み中…

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