Hydrogen chloride-ethyl acetate → HCID 86631007, 화합물

HRID 2070532노트

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HRID 2070532 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:18]([S:19]([C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)(=[O:21])=[O:20])[CH:17]=[C:16]([CH2:28][N:29](C)[C:30](=O)OC(C)(C)C)[CH:15]=3)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C(OCC)(=O)C.Cl>C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:18]([S:19]([C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)(=[O:21])=[O:20])[CH:17]=[C:16]([CH2:28][NH:29][CH3:30])[CH:15]=3)=[CH:10][N:9]=2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86631003HCID 86631003, 화합물

생성물 1

HCID 86631007HCID 86631007, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
70 °C

실험 절차

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%).

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. customThe residue was purified by basic silica gel column chromatography (eluent: ethyl acetate-methanol=99:1→19:1)

출처 및 근거

ORD 기록
ord-9dbf5411fb9b4e3a84855f0b179d634b
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299261B2

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