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

HRID 869778Notes

Reaction equation

HRID 869778 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][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])[CH2:2][CH2:3][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 1110Succinic AcidHCID 446344821-{4-Fluoro-5-(2-fluoropyridin-3-yl)-1-[(4-methylpyridin-2-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine

Product 1

HCID 671771231-{4-Fluoro-5-(2-fluoropyridin-3-yl)-1-[(4-methylpyridin-2-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine succinateYield 93.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of succinic acid (59 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-water to give the title compound as a white solid (yield 232 mg, 93%).

Workup

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

Sources & evidence

ORD record
ord-c322b8b641ea4b8496aef7dd6d48da3b
Source dataset
uspto-grants-2015_03
Patent number
US08969387B2

Reaction notes

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