Acetic Acid → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzothiophene-2-carboxamide dihydrochloride

HRID 335601ノート

反応式

HRID 335601 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[S:14][C:15]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:16]=3[CH:17]=1)=[O:12])[CH2:3]2.C(O)(=O)C>[Zn].O>[ClH:1].[ClH:1].[N:2]12[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]1)[C@@H:4]([NH:10][C:11]([C:13]1[S:14][C:15]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:16]=3[CH:17]=1)=[O:12])[CH2:3]2

参加物

5

反応物 2

HCID 176Acetic AcidHCID 68429753N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzothiophene-2-carboxamide hydrochloride

生成物 1

HCID 68431067N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzothiophene-2-carboxamide dihydrochloride

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 962Water溶媒

実験手順

385.0 mg (1.05 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-5-nitro-1-benzothio-phene-2-carboxamide hydrochloride are suspended in 10 ml of a 1:1 mixture of acetic acid and water. 300.0 mg (4.59 mmol) of zinc are added, and the mixture is then stirred at RT for 1 h. The reaction mixture is filtered through kieselguhr, and the filter cake is washed with methanol. The filtrate is concentrated under reduced pressure and the residue is purified by preparative HPLC. The product fraction is dissolved in 4M HCl in dioxane, concentrated under reduced pressure and recrystallized from acetonitrile. 233 mg (59.5% of theory) of the title compound are obtained.

後処理

  1. filtrationThe reaction mixture is filtered through kieselguhr
  2. washthe filter cake is washed with methanol
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. customthe residue is purified by preparative HPLC
  5. dissolutionThe product fraction is dissolved in 4M HCl in dioxane
  6. concentrationconcentrated under reduced pressure
  7. customrecrystallized from acetonitrile

出典と根拠

ORDレコード
ord-0dd8b884a894433fb11aba8b453b0e93
出典データセット
uspto-grants-2014_11
特許番号
US08884017B2

反応ノート

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