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Sodium hydride → N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-(2-chloro-pyridin-4-yloxy)-4-methyl-benzamide

HRID 1844595
ノート
印刷プレビュー

反応式

HRID 1844595 の反応式
[H-].[Na+].[C:3]([C:7]1[CH:8]=[C:9]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:10]([O:24][CH3:25])=[C:11]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([OH:22])[CH:16]=2)[CH:12]=1)([CH3:6])([CH3:5])[CH3:4].[H][H].[Cl:33][C:34]1[CH:39]=[C:38](I)[CH:37]=[CH:36][N:35]=1>CN(C)C=O>[C:3]([C:7]1[CH:8]=[C:9]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[C:10]([O:24][CH3:25])=[C:11]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[C:17]([O:22][C:38]3[CH:37]=[CH:36][N:35]=[C:34]([Cl:33])[CH:39]=3)[CH:16]=2)[CH:12]=1)([CH3:6])([CH3:4])[CH3:5]
参加物反応条件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 24758Sodium hydrideHCID 15165112-Chloro-4-iodopyridineHCID 67217566N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-hydroxy-4-methyl-benzamideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 86664520N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-(2-chloro-pyridin-4-yloxy)-4-methyl-benzamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

545 mg sodium hydride (60% in mineral oil) are added to 2.77 g N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-hydroxy-4-methyl-benzamide in 15 ml N,N-dimethylformamide under an argon atmosphere and while cooling with an ice bath, and the reaction mixture is stirred at ambient temperature until no further hydrogen development can be detected. Then 1.63 g 2-chloro-4-iodopyridine are added, and the reaction mixture is stirred overnight at 110° C. After cooling to ambient temperature the solvent is distilled off using the rotary evaporator. The flask residue is taken up in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution, dried on magnesium sulphate and evaporated down. The flask residue is chromatographed through a silica gel column with petroleum ether/ethyl acetate (80:20→30:70) as eluant. The product is stirred with diethyl ether, suction filtered and dried.

後処理

  1. temperaturewhile cooling with an ice bath
  2. temperatureAfter cooling to ambient temperature the solvent
  3. distillationis distilled off
  4. customthe rotary evaporator
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  6. customdried on magnesium sulphate
  7. customevaporated down
  8. customThe flask residue is chromatographed through a silica gel column with petroleum ether/ethyl acetate (80:20→30:70) as eluant
  9. stirringThe product is stirred with diethyl ether, suction
  10. filtrationfiltered
  11. customdried

出典と根拠

ORDレコード
ord-cef0cfca89f1418ba39922e9576945b5
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946438B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート