Hydrogen chloride-ethyl acetate → HCID 86631007, compound

HRID 1012553Notes

Reaction equation

HRID 1012553 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 86631007HCID 86631007, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-479c40c3af2741d8b72f83df096eead6
Source dataset
uspto-grants-2011_07
Patent number
US07977488B2

Reaction notes

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