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

HRID 1962660노트

반응식

HRID 1962660 반응식
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

참가 물질

4

반응물 3

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

생성물 1

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

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온도
70 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-5e38b9f7bd274981b026df9e0d67d859
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415368B2

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