Methanol → 1-[5-(2-fluoro-6-methoxyphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine Fumarate

HRID 1782385Notes

Reaction equation

HRID 1782385 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[N:14]([S:15]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:13]=[C:12]([CH2:24][N:25](C)[C:26](=O)[O:27][C:28]([CH3:31])(C)C)[CH:11]=1.[C:34]([O:37]CC)(=[O:36])[CH3:35].Cl.C[OH:42]>>[C:28]([OH:42])(=[O:27])/[CH:31]=[CH:35]/[C:34]([OH:37])=[O:36].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[N:14]([S:15]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH:13]=[C:12]([CH2:24][NH:25][CH3:26])[CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 66974539tert-butyl{[5-(2-fluoro-6-methoxyphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

Product 1

HCID 669746531-[5-(2-fluoro-6-methoxyphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine FumarateYield 51%

Conditions

Temperature
70 °C

Procedure

tert-Butyl {[5-(2-fluoro-6-methoxyphenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (100 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 dissolved in ethanol (6 mL), fumaric acid (49 mg) was added, and the obtained crystals were collected by filtration to give the title compound as colorless crystals (yield 53 mg, 51%).

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. dissolutionThe residue was dissolved in ethanol (6 mL)
  8. additionfumaric acid (49 mg) was added
  9. filtrationthe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-b83f256db5e847eeb9a99bc63b0ddc29
Source dataset
uspto-grants-2009_03
Patent number
US07498337B2

Reaction notes

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