Ethanol → 1-[5-(2-chloropyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Fumarate

HRID 1962660ノート

反応式

HRID 1962660 の反応式
C([O:5][C:6](=[O:31])[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([C:15]2[C:16]([Cl:21])=[N:17][CH:18]=[CH:19][CH:20]=2)[N:12]([S:22]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)(=[O:24])=[O:23])[CH:11]=1)C)(C)(C)C.[C:32]([O:35]CC)(=[O:34])[CH3:33].Cl.[CH2:39](O)C>>[C:6]([OH:5])(=[O:31])/[CH:39]=[CH:33]/[C:32]([OH:35])=[O:34].[Cl:21][C:16]1[C:15]([C:13]2[N:12]([S:22]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)(=[O:23])=[O:24])[CH:11]=[C:10]([CH2:9][NH:7][CH3:6])[CH:14]=2)=[CH:20][CH:19]=[CH:18][N:17]=1

参加物

4

反応物 3

HCID 702EthanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 86623987tert-butyl {[5-(2-chloropyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

生成物 1

HCID 866310061-[5-(2-chloropyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Fumarate収率 68%

反応条件

温度
70 °C

実験手順

tert-Butyl{[5-(2-chloropyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (280 mg) was dissolved in ethanol (10 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 dissolved in ethyl acetate (10 mL), a solution of fumaric acid (116 mg) in methanol (3 mL) was added, and the obtained crystals were collected by filtration to give the title compound as colorless crystals (yield 197 mg, 68%).

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. dissolutionThe residue was dissolved in ethyl acetate (10 mL)
  7. additiona solution of fumaric acid (116 mg) in methanol (3 mL) was added
  8. filtrationthe obtained crystals were collected by filtration

出典と根拠

ORDレコード
ord-5e38b9f7bd274981b026df9e0d67d859
出典データセット
uspto-grants-2013_04
特許番号
US08415368B2

反応ノート

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