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 2047938Notes

Reaction equation

HRID 2047938 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-f0e805a3654c4bcdb0c794ee4b731353
Source dataset
uspto-grants-2013_11
Patent number
US08592597B2

Reaction notes

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