Hydrogen chloride-ethyl acetate → HCID 86631007, Verbindung

HRID 2197058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2197058
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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 86631007HCID 86631007, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-0c50be5363e64eb3b9cae8d72a380e20
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338461B2

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