Sodium Hydroxide → 5-HT3 antagonist 1

HRID 2051180노트

반응식

HRID 2051180 반응식
[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

참가 물질

7

반응물 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

생성물 1

HCID 104072565-HT3 antagonist 1수율 32.4%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c2af7703fc284f0dad98c7ff468ed563
출처 데이터셋
uspto-grants-1991_05
특허 번호
US05017573

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