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Methanol → 1-[5-(3-fluoropyridin-4-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Fumarate

HRID 2197056
ノート
印刷プレビュー

反応式

HRID 2197056 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[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[F:21])[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.[CH3:39]O>>[C:6]([OH:5])(=[O:31])/[CH:39]=[CH:33]/[C:32]([OH:35])=[O:34].[F:21][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:15]=1[C:13]1[N:12]([S:22]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)(=[O:24])=[O:23])[CH:11]=[C:10]([CH2:9][NH:7][CH3:6])[CH:14]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 3

HCID 887MethanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 66974615tert-butyl {[5-(3-fluoropyridin-4-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

生成物 1

HCID 669747671-[5-(3-fluoropyridin-4-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Fumarate収率 72%

反応条件

温度
70 °C

実験手順

tert-Butyl{[5-(3-fluoropyridin-4-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (60 mg) was dissolved in methanol (5 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (1.5 mL) was added and the mixture was stirred at 70° C. for 30 min. The reaction mixture was concentrated under reduced pressure and a saturated aqueous sodium hydrogencarbonate solution was added. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (8 mL), a solution of fumaric acid (58 mg) in methanol (2 mL) was added, and the obtained crystals were collected by filtration to give the title compound as colorless crystals (yield 45 mg, 72%).

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. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate (8 mL)
  8. additiona solution of fumaric acid (58 mg) in methanol (2 mL) was added
  9. filtrationthe obtained crystals were collected by filtration

出典と根拠

ORDレコード
ord-ac1bba1d3dc4437a9a384065ed2c9e8f
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08338461B2

反応ノート

読み込み中…

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