Stannous Chloride → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-amino-1-benzofuran-2-carboxamide

HRID 335591

반응식

HRID 335591 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[C:23]([N+:24]([O-])=O)=[CH:22][CH:21]=[CH:20][C:18]=3[CH:19]=1)=[O:14])[CH2:5]2>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[C:23]([NH2:24])=[CH:22][CH:21]=[CH:20][C:18]=3[CH:19]=1)=[O:14])[CH2:5]2

참가 물질

4

반응물 2

HCID 24479Stannous ChlorideHCID 59341430N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-nitro-1-benzofuran-2-carboxamide

생성물 1

HCID 59341406N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-7-amino-1-benzofuran-2-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6.0 ml (12 mmol) of a 2 M tin(II) chloride solution in DMF are added to N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-nitro-1-benzofuran-2-carboxamide (1340 mg, 4.25 mmol). The mixture is stirred overnight. The solvent is removed under reduced pressure using a rotary evaporator. The crude product is taken up in methanol and, together with acidic ion exchange resin (Dowex WX2-200), shaken for about 1 h. The loaded ion exchanger is washed with methanol, then with water, again with methanol, with DMF, again with methanol, with THF, again with methanol, with dichloromethane and finally once more with methanol. The product is eluted with methanol/triethylamine 95:5. The solvent is removed under reduced pressure using a rotary evaporator. 1200 mg (98% of theory) of the title compound are obtained.

후처리

  1. customThe solvent is removed under reduced pressure
  2. customa rotary evaporator
  3. stirringshaken for about 1 h
  4. washThe loaded ion exchanger is washed with methanol
  5. washThe product is eluted with methanol/triethylamine 95:5
  6. customThe solvent is removed under reduced pressure
  7. customa rotary evaporator

출처 및 근거

ORD 기록
ord-3e4bf6b604ba4fb2b9d0a2ae38dcff94
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08884017B2

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