Pyridine → N-(4-methoxyphenyl)-2-[[1-(4-pyridyl)piperidin-4-ylcarbonyl]amino]benzamide

HRID 395790

反応式

HRID 395790 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:15][CH2:14][CH:10]([C:11]([OH:13])=O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.S(Cl)(Cl)=O.[NH2:20][C:21]1[CH:37]=[CH:36][CH:35]=[CH:34][C:22]=1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)=[O:24].N1C=CC=CC=1>ClCCl>[CH3:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([NH:25][C:23](=[O:24])[C:22]2[CH:34]=[CH:35][CH:36]=[CH:37][C:21]=2[NH:20][C:11]([CH:10]2[CH2:9][CH2:8][N:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH2:15][CH2:14]2)=[O:13])=[CH:31][CH:30]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 4788202-amino-N-(4-methoxyphenyl)benzamideHCID 12682891-(Pyridin-4-yl)piperidine-4-carboxylic acid

生成物 1

HCID 18174545N-(4-methoxyphenyl)-2-[[1-(4-pyridyl)piperidin-4-ylcarbonyl]amino]benzamide収率 30.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred suspension of N-(4-pyridyl)isonipecotic acid (0.2 g, 1 mmol) in dichloromethane (70 mL) was added thionyl chloride (0.11 mL, 1.5 mmol). After stirring overnight, the solvent was removed in vacuo and the residue was dissolved in dichloromethane (10 mL) and added to a stirred solution of 2-amino-N-(4-methoxyphenyl)benzamide (0.186 g, 0.77 mmol) and pyridine (0.19 g, 0.85 mmol) in dichloromethane (25 mL). After stirring for 72 h, the solution was transferred to a separatory funnel and washed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. The organic phase was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was suspended in a mixture of diethyl ether and hexanes, sonicated, and filtered. The resulting solid was washed with diethyl ether and dried in vacuo to give 0.10 g (30%) of the title compound as a pale tan solid.

後処理

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane (10 mL)
  3. stirringAfter stirring for 72 h
  4. customthe solution was transferred to a separatory funnel
  5. washwashed with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  6. dry with materialThe organic phase was dried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionThe residue was suspended in a mixture of diethyl ether and hexanes
  10. customsonicated
  11. filtrationfiltered
  12. washThe resulting solid was washed with diethyl ether
  13. customdried in vacuo

出典と根拠

ORDレコード
ord-7ac8badbfd9c4996afebd2dc23dd7fda
出典データセット
uspto-grants-2003_08
特許番号
US06605626B2

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