Sodium Hydroxide → 5-HT3 antagonist 1

HRID 374101ノート

反応式

HRID 374101 の反応式
[C:1]([NH:4][CH:5]1[CH2:11][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=2)[CH2:9][CH2:8][N:7]([CH3:20])[CH2:6]1)(=[O:3])[CH3:2].[OH-].[Na+].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)C(C(O)=O)=[N:24]1.Cl.C(N=C=NCCCN(C)C)C>Cl.ClCCl>[CH3:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][N:10]1[CH2:11][CH:5]([NH:4][C:1]([C:2]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:23][N:24]=2)=[O:3])[CH2:6][N:7]([CH3:20])[CH2:8][CH2:9]1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 78250Indazole-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 149989916-acetylamino-1-(3-methylbenzyl)-4-methylhexahydro-1H-1,4-diazepine

生成物 1

HCID 104072565-HT3 antagonist 1収率 32.4%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 6-acetylamino-1-(3-methylbenzyl)-4-methyl-hexahydro-1H-1,4-diazepine (0.9 g) in 10% hydrochloric acid (20 ml) is refluxed with stirring for 2 hours. After cooling, the reaction mixture is basified with 48% aqueous sodium hydroxide solution and extracted with chloroform. The organic layer is washed with water and dried over magnesium sulfate. The solvent is evaporated under reduced pressure to give an oil. A mixture of this oil, 1H-indazole-3-carboxylic acid (530 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (630 mg) and dichloromethane (20 ml) is stirred at 25° C. for 2 hours. The reaction mixture is washed successively with water and 10% aqueous sodium hydroxide solution, dried over magnesium sulfate, and evaporated under reduced pressure. The residue is chromatographed on silica gel with elution of acetone. Fractions containing the title compound are pooled and evaporated under reduced pressure to give the title compound (0.4 g) as an oil.

後処理

  1. temperatureAfter cooling
  2. extractionextracted with chloroform
  3. washThe organic layer is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is evaporated under reduced pressure
  6. customto give an oil
  7. stirringis stirred at 25° C. for 2 hours
  8. washThe reaction mixture is washed successively with water and 10% aqueous sodium hydroxide solution
  9. dry with materialdried over magnesium sulfate
  10. customevaporated under reduced pressure
  11. customThe residue is chromatographed on silica gel with elution of acetone
  12. additionFractions containing the title compound
  13. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-74f6d78a7c7f40ab8d1342a521befe3b
出典データセット
uspto-grants-1992_11
特許番号
US05166341

反応ノート

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