Methanol → HCID 66974400, compound

HRID 1782386Notes

Reaction equation

HRID 1782386 reaction equation
[CH3:1][N:2]([CH2:10][C:11]1[CH:15]=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:21]=2[CH3:22])[N:13]([S:23]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)(=[O:25])=[O:24])[CH:12]=1)C(=O)[O:4][C:5]([CH3:8])(C)C.[C:32]([O:35]CC)(=[O:34])[CH3:33].Cl.C[OH:40]>>[C:5]([OH:4])(=[O:40])/[CH:8]=[CH:33]/[C:32]([OH:35])=[O:34].[CH3:1][NH:2][CH2:10][C:11]1[CH:15]=[C:14]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:21]=2[CH3:22])[N:13]([S:23]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)(=[O:24])=[O:25])[CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 66974699HCID 66974699, compound

Product 1

HCID 66974400HCID 66974400, compound

Conditions

Temperature
70 °C

Procedure

tert-Butyl methyl{[5-(4-methylpyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}carbamate (230 mg) was dissolved in methanol (20 mL), a 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added and the mixture was stirred at 70° C. for 20 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 obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate-methanol (99:1→95:5) to give a free salt of the title compound. This was dissolved in ethyl acetate (8 mL), a solution of fumaric acid (90 mg) in methanol (2 mL) was added, and the obtained crystals were collected by filtration to give the title compound as colorless crystals (yield 115 mg, 48%).

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 obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-9a8710ed5398494381e381d5acd99f98
Source dataset
uspto-grants-2009_03
Patent number
US07498337B2

Reaction notes

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