Hydrogen chloride-ethyl acetate → HCID 86631007、化合物

HRID 1012553ノート

反応式

HRID 1012553 の反応式
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:22]=[N:23][C:24]([Cl:27])=[CH:25][CH:26]=3)=[N:19][CH:20]=2)[N:12]([S:28]([C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)(=[O:30])=[O:29])[CH:11]=1)C)(C)(C)C.C(OCC)(=O)C.Cl>C(O)C>[Cl:27][C:24]1[N:23]=[CH:22][C:21]([C:18]2[CH:17]=[CH:16][C:15]([C:13]3[N:12]([S:28]([C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)(=[O:30])=[O:29])[CH:11]=[C:10]([CH2:9][NH:7][CH3:6])[CH:14]=3)=[CH:20][N:19]=2)=[CH:26][CH:25]=1

参加物

4

反応物 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86631003HCID 86631003、化合物

生成物 1

HCID 86631007HCID 86631007、化合物

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

tert-Butyl{[5-(6′-chloro-2,3′-bipyridin-5-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (100 mg) was dissolved in ethanol (8 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added and the mixture was stirred at 70° C. for 30 min. The reaction mixture was concentrated under reduced pressure, a saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=99:1→19:1) to give a free salt of the title compound. The obtained free salt was dissolved in ethyl acetate (8 mL), a solution of fumaric acid (116 mg) in methanol (2 mL) was added, and the obtained crystals were collected by filtration to give the title compound as colorless crystals (yield 61 mg, 66%).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogencarbonate solution was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (eluent:ethyl acetate-methanol=99:1→19:1)

出典と根拠

ORDレコード
ord-479c40c3af2741d8b72f83df096eead6
出典データセット
uspto-grants-2011_07
特許番号
US07977488B2

反応ノート

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