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

HRID 1426780Notes

Reaction equation

HRID 1426780 reaction equation
[F:1][C:2]1[C:7]([C:8]2[N:12]([S:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:22][N:23](C)[C:24](=O)[O:25][C:26]([CH3:29])(C)C)[CH:9]=2)=[CH:6][CH:5]=[C:4]([CH3:32])[N:3]=1.[C:33]([O:36]CC)(=[O:35])[CH3:34].Cl.C[OH:41]>>[C:26]([OH:25])(=[O:41])/[CH:29]=[CH:34]/[C:33]([OH:36])=[O:35].[F:1][C:2]1[C:7]([C:8]2[N:12]([S:13]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)(=[O:14])=[O:15])[CH:11]=[C:10]([CH2:22][NH:23][CH3:24])[CH:9]=2)=[CH:6][CH:5]=[C:4]([CH3:32])[N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 21866389Hydrogen chloride-ethyl acetateHCID 67397434tert-butyl {[5-(2-fluoro-6-methylpyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

Product 1

HCID 673972381-[5-(2-fluoro-6-methylpyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine fumarateYield 64%

Conditions

Temperature
60 °C

Procedure

tert-Butyl {[5-(2-fluoro-6-methylpyridin-3-yl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate (400 mg) was dissolved in methanol (20 mL), 4 mol/L hydrogen chloride-ethyl acetate solution (2 mL) was added, and the mixture was stirred at 60° C. for 10 min. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate 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 crystallized from a mixed solution of fumaric acid (101 mg), methanol (3 mL) and ethyl acetate (12 mL) to give the title compound as colorless crystals (yield 264 mg, 64%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution
  2. additionwas 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 crystallized from a mixed solution of fumaric acid (101 mg), methanol (3 mL) and ethyl acetate (12 mL)

Sources & evidence

ORD record
ord-30975a9a41c74a8ea9740c339cd3582f
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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