p-Toluenesulfonate → Sorafenib Tosylate

HRID 332936

Reaction equation

HRID 332936 reaction equation
[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-:4])(=[O:3])=[O:2].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]2[CH:39]=[CH:38][C:26]([O:27][C:28]3[CH:33]=[CH:32][N:31]=[C:30]([C:34]([NH:36][CH3:37])=[O:35])[CH:29]=3)=[CH:25][CH:24]=2)=[O:21])=[CH:15][C:14]=1[C:40]([F:43])([F:42])[F:41]>CO>[S:1]([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([OH:4])(=[O:3])=[O:2].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]2[CH:39]=[CH:38][C:26]([O:27][C:28]3[CH:33]=[CH:32][N:31]=[C:30]([C:34]([NH:36][CH3:37])=[O:35])[CH:29]=3)=[CH:25][CH:24]=2)=[O:21])=[CH:15][C:14]=1[C:40]([F:43])([F:41])[F:42]

Participants

4

Reactant 2

HCID 85570p-ToluenesulfonateHCID 216239Sorafenib

Product 1

HCID 406563Sorafenib Tosylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.5 g of the tosylate salt of 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)-amino]phenoxy}-N-methylpyridine-2-carboxamide in the polymorph II are suspended in 15 ml of methanol and stirred at room temperature. After one week, the suspension is filtered and the residue dried at room temperature. Subsequently, the product is heat-treated at 150° C. for 30 min. The residue is analyzed by X-ray diffractometry and corresponds to the title compound in the polymorph III.

Workup

  1. waitAfter one week
  2. filtrationthe suspension is filtered
  3. customthe residue dried at room temperature
  4. additionSubsequently, the product is heat-treated at 150° C. for 30 min

Sources & evidence

ORD record
ord-21e034fe98d94e6bb1f2b10d3807ccd0
Source dataset
uspto-grants-2014_11
Patent number
US08877933B2

Linked notes

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