L-Tartaric acid → 1-{4-Fluoro-5-(2-fluoropyridin-3-yl)-1-[(5-fluoropyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine L-tartrate

HRID 869780Notes

Reaction equation

HRID 869780 reaction equation
[C:1]([OH:10])(=[O:9])[C@@H:2]([C@H:4]([C:6]([OH:8])=[O:7])[OH:5])[OH:3].[F:11][C:12]1[C:13]([CH2:34][NH:35][CH3:36])=[CH:14][N:15]([S:24]([C:27]2[CH:28]=[N:29][CH:30]=[C:31]([F:33])[CH:32]=2)(=[O:26])=[O:25])[C:16]=1[C:17]1[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=1>C(O)C>[C:6]([C@@H:4]([C@H:2]([C:1]([OH:10])=[O:9])[OH:3])[OH:5])([OH:8])=[O:7].[F:11][C:12]1[C:13]([CH2:34][NH:35][CH3:36])=[CH:14][N:15]([S:24]([C:27]2[CH:28]=[N:29][CH:30]=[C:31]([F:33])[CH:32]=2)(=[O:25])=[O:26])[C:16]=1[C:17]1[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 671770021-(4-fluoro-5-(2-fluoropyridin-3-yl)-1-[(5-fluoropyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl)-N-methylmethanamine

Product 1

HCID 671778061-{4-Fluoro-5-(2-fluoropyridin-3-yl)-1-[(5-fluoropyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine L-tartrateYield 88.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of L-tartaric acid (59 mg) in ethanol (4 mL) was added to 1-{4-fluoro-5-(2-fluoropyridin-3-yl)-1-[(5-fluoropyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}-N-methylmethanamine (150 mg), and the mixture was concentrated under reduced pressure. The residue was recrystallized from ethanol to give the title compound as a white solid (yield 184 mg, 88%).

Workup

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

Sources & evidence

ORD record
ord-ab34fe82846649d7bb0b48f2e724f4a1
Source dataset
uspto-grants-2015_03
Patent number
US08969387B2

Reaction notes

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