Fumaric Acid → 1-{4-Fluoro-5-(2-fluoropyridin-3-yl)-1-[(4-methylpyridin-2-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine fumarate

HRID 2047939Notes

Reaction equation

HRID 2047939 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[F:9][C:10]1[C:11]([CH2:32][NH:33][CH3:34])=[CH:12][N:13]([S:22]([C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=2)(=[O:24])=[O:23])[C:14]=1[C:15]1[C:16]([F:21])=[N:17][CH:18]=[CH:19][CH:20]=1>C(O)C.C(OCC)(=O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[F:9][C:10]1[C:11]([CH2:32][NH:33][CH3:34])=[CH:12][N:13]([S:22]([C:25]2[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=2)(=[O:24])=[O:23])[C:14]=1[C:15]1[C:16]([F:21])=[N:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 446344821-{4-Fluoro-5-(2-fluoropyridin-3-yl)-1-[(4-methylpyridin-2-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine

Product 1

HCID 671771951-{4-Fluoro-5-(2-fluoropyridin-3-yl)-1-[(4-methylpyridin-2-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine fumarateYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of fumaric acid (58 mg) in ethanol (2 mL) was added a solution of 1-{4-fluoro-5-(2-fluoropyridin-3-yl)-1-[(4-methylpyridin-2-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine (189 mg) in ethyl acetate (2 mL), and the mixture was concentrated under reduced pressure. The residue was recrystallized from ethanol to give the title compound as a white solid (yield 224 mg, 91%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-5f09615f2ec9455588a09825057f6ba6
Source dataset
uspto-grants-2013_11
Patent number
US08592597B2

Reaction notes

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