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

HRID 335591

反応式

HRID 335591 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3e4bf6b604ba4fb2b9d0a2ae38dcff94
出典データセット
uspto-grants-2014_11
特許番号
US08884017B2

関連ノート

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