Water → N6-Methoxy-4-(4-amino-3-chlorophenoxy)-7-benzyloxy-6-quinolinecarboxamide

HRID 1433741ノート

反応式

HRID 1433741 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9].[H-].[Na+].[CH3:12][O:13][NH:14][C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[N:23]=[CH:22][CH:21]=[C:20]2Cl)=[O:16].O>CS(C)=O.C(OCC)(=O)C.CCCCCC>[CH3:12][O:13][NH:14][C:15]([C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:26]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[N:23]=[CH:22][CH:21]=[C:20]2[O:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[C:3]([Cl:9])[CH:4]=1)=[O:16]

参加物

8

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 871844-Amino-3-chlorophenolHCID 22936829N6-Methoxy-7-benzyloxy-4-chloro-6-quinolinecarboxamide

生成物 1

HCID 22936373N6-Methoxy-4-(4-amino-3-chlorophenoxy)-7-benzyloxy-6-quinolinecarboxamide収率 16%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
100 °C

実験手順

After dissolving 4-amino-3-chlorophenol (408 mg, 2.84 mmol) in dimethylsulfoxide (10 ml), sodium hydride (114 mg, 2.84 mmol) was gradually added at room temperature and the mixture was stirred for 30 minutes. N6-Methoxy-7-benzyloxy-4-chloro-6-quinolinecarboxamide (388 mg, 1.14 mmol) was added, and the mixture was heated at 100° C. for 18 hours while stirring. Upon cooling to room temperature, the reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. After distilling off the solvent, it was subjected to silica gel column chromatography, the target fraction was concentrated under reduced pressure, the obtained crude product was suspended in ethyl acetate, the suspension was diluted with hexane, and the crystals were filtered out, washed with hexane and blow-dried to obtain the title compound (81.0 mg, 0.180 mmol, 16%) as light red crystals.

後処理

  1. additionwas gradually added at room temperature
  2. stirringwhile stirring
  3. temperatureUpon cooling to room temperature
  4. washthe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter distilling off the solvent, it
  7. concentrationthe target fraction was concentrated under reduced pressure
  8. customthe obtained crude product
  9. filtrationthe crystals were filtered out
  10. washwashed with hexane
  11. customblow-dried

出典と根拠

ORDレコード
ord-d4996f92737d4550baf30b400c64c34d
出典データセット
uspto-grants-2009_11
特許番号
US07612092B2

反応ノート

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