Sodium Hydroxide → HCID 10237474、化合物

HRID 15455ノート

反応式

HRID 15455 の反応式
[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@@H:4]([NH:10][C:11]([C:13]1[O:14][C:15]3[C:21]([O:22][CH3:23])=[CH:20][C:19]([N+:24]([O-])=O)=[CH:18][C:16]=3[CH:17]=1)=[O:12])[CH2:3]2.[OH-].[Na+].C([O-])=O.[NH4+]>C(OCC)(=O)C>[ClH:1].[ClH:1].[NH2:24][C:19]1[CH:20]=[C:21]([O:22][CH3:23])[C:15]2[O:14][C:13]([C:11]([NH:10][C@@H:4]3[CH:5]4[CH2:6][CH2:7][N:2]([CH2:9][CH2:8]4)[CH2:3]3)=[O:12])=[CH:17][C:16]=2[CH:18]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 2723923Ammonium formateHCID 68429848N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-methoxy-5-nitro-1-benzofuran-2-carboxamide hydrochloride

生成物 1

HCID 10237474HCID 10237474、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

Initially, N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-methoxy-5-nitro-1-benzofuran-2-carboxamide hydrochloride (120 mg, 0.31 mmol) is converted into the free base. To this end, the compound is taken up in ethyl acetate, and 30% strength aqueous sodium hydroxide solution is added. The aqueous phase is extracted repeatedly with ethyl acetate. The extract is dried over magnesium sulfate and the solvent is removed under reduced pressure. The free base is dissolved in 3 ml of methanol. 120 mg (1.84 mmol) of ammonium formate are added, and the mixture is heated under reflux for 4 h. The reaction mixture is filtered through Celite, and the filter cake is washed with ethanol and ethyl acetate. The crude product is subjected to fine purification on silica gel 60 (mobile phase: dichloromethane→dichloromethane/methanol 10:1→dichloromethane/methanol/ammonia 80:20:2). An excess of 4N HCl in dioxane is added to the free base. The solvent is then removed under reduced pressure. 25 mg (17% of theory) of the title compound are isolated.

後処理

  1. extractionThe aqueous phase is extracted repeatedly with ethyl acetate
  2. dry with materialThe extract is dried over magnesium sulfate
  3. customthe solvent is removed under reduced pressure
  4. dissolutionThe free base is dissolved in 3 ml of methanol
  5. temperaturethe mixture is heated
  6. temperatureunder reflux for 4 h
  7. filtrationThe reaction mixture is filtered through Celite
  8. washthe filter cake is washed with ethanol and ethyl acetate
  9. customThe crude product is subjected to fine purification on silica gel 60 (mobile phase: dichloromethane→dichloromethane/methanol 10:1→dichloromethane/methanol/ammonia 80:20:2)
  10. additionAn excess of 4N HCl in dioxane is added to the free base
  11. customThe solvent is then removed under reduced pressure

出典と根拠

ORDレコード
ord-290ea0447d204eddb847c7753aff8c55
出典データセット
uspto-grants-2010_06
特許番号
US07732477B2

反応ノート

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