Water → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzofuran-2-carboxamide

HRID 658190

반응식

HRID 658190 반응식
[Sn](Cl)Cl.[N:4]12[CH2:11][CH2:10][CH:7]([CH2:8][CH2:9]1)[C@@H:6]([NH:12][C:13]([C:15]1[O:16][C:17]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:18]=3[CH:19]=1)=[O:14])[CH2:5]2.O.[OH-].[Na+]>CN(C=O)C>[N:4]12[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11]1)[C@@H:6]([NH:12][C:13]([C:15]1[O:16][C:17]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:18]=3[CH:19]=1)=[O:14])[CH2:5]2

참가 물질

6

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 59341432N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzofuran-2-carboxamide

생성물 1

HCID 10236388N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzofuran-2-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2.0 ml (4 mmol) of a 2 M tin(II) chloride solution in DMF are added to N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzofuran-2-carboxamide (100 mg, 0.32 mmol). The mixture is stirred overnight. The reaction mixture is poured into water and made basic using 1N aqueous sodium hydroxide solution. The aqueous phase is extracted six times with ethyl acetate. The combined organic phases are dried over magnesium sulfate, and the solvent is removed under reduced pressure using a rotary evaporator. The crude product is taken up in methanol and shaken together with acidic ion exchange resin (Dowex WX2-200) for about 20 min. The loaded ion exchanger is washed three times with in each ase 30 ml of methanol, then with water/methanol 8:2, again with methanol, with dichloromethane and finally again with methanol. The product is eluted using methanol/triethylamine 95:5. The solvent is removed under reduced pressure using a rotary evaporator. 52 mg (58% of theory) of the title compound are isolated.

후처리

  1. extractionThe aqueous phase is extracted six times with ethyl acetate
  2. dry with materialThe combined organic phases are dried over magnesium sulfate
  3. customthe solvent is removed under reduced pressure
  4. customa rotary evaporator
  5. stirringshaken together with acidic ion exchange resin (Dowex WX2-200) for about 20 min
  6. washThe loaded ion exchanger is washed three times with in each ase 30 ml of methanol
  7. washThe product is eluted
  8. customThe solvent is removed under reduced pressure
  9. customa rotary evaporator

출처 및 근거

ORD 기록
ord-d3fb09c5c8384443a378647a8ad36b27
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076355B2

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