1-{4-Fluoro-5-(2-fluoropyridin-3-yl)-1-[(5-fluoropyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine hydrochloride → 1-(4-fluoro-5-(2-fluoropyridin-3-yl)-1-[(5-fluoropyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl)-N-methylmethanamine

HRID 869776Notes

Reaction equation

HRID 869776 reaction equation
Cl.[F:2][C:3]1[C:4]([CH2:25][NH:26][CH3:27])=[CH:5][N:6]([S:15]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([F:24])[CH:23]=2)(=[O:17])=[O:16])[C:7]=1[C:8]1[C:9]([F:14])=[N:10][CH:11]=[CH:12][CH:13]=1>C(=O)([O-])O.[Na+]>[F:2][C:3]1[C:4]([CH2:25][NH:26][CH3:27])=[CH:5][N:6]([S:15]([C:18]2[CH:19]=[N:20][CH:21]=[C:22]([F:24])[CH:23]=2)(=[O:16])=[O:17])[C:7]=1[C:8]1[C:9]([F:14])=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 671772671-{4-Fluoro-5-(2-fluoropyridin-3-yl)-1-[(5-fluoropyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine hydrochloride

Product 1

HCID 671770021-(4-fluoro-5-(2-fluoropyridin-3-yl)-1-[(5-fluoropyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl)-N-methylmethanamineYield 87%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

1-{4-Fluoro-5-(2-fluoropyridin-3-yl)-1-[(5-fluoropyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine hydrochloride (780 mg) was dissolved in saturated aqueous sodium hydrogen carbonate, and the mixture was extracted twice with ethyl acetate. Combined organic layers were 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: hexane-ethyl acetate=3:1→3:7) to give the title compound as a pale-yellow oil (yield 619 mg, 87%).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washCombined organic layers were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=3:1→3:7)

Sources & evidence

ORD record
ord-78af54ccdc2849bebd68acfce4bdec40
Source dataset
uspto-grants-2015_03
Patent number
US08969387B2

Reaction notes

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