Sorafenib → Sorafenib Tosylate

HRID 332935

Reaction equation

HRID 332935 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:28]=[CH:27][C:15]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([C:23]([NH:25][CH3:26])=[O:24])[CH:18]=3)=[CH:14][CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:29]([F:32])([F:31])[F:30].O.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(O)C>[S:40]([C:37]1[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=1)([OH:43])(=[O:42])=[O:41].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:28]=[CH:27][C:15]([O:16][C:17]3[CH:22]=[CH:21][N:20]=[C:19]([C:23]([NH:25][CH3:26])=[O:24])[CH:18]=3)=[CH:14][CH:13]=2)=[O:10])=[CH:4][C:3]=1[C:29]([F:32])([F:30])[F:31]

Participants

4

Reactant 2

HCID 216239SorafenibHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 406563Sorafenib TosylateYield 91.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

903 g of 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-N-methyl-pyridine-2-carboxamide, prepared as described in WO 00/42012, are initially charged in 2700 ml of ethanol. 451.7 g of p-toluenesulfonic acid monohydrate are dissolved in 1340 g of ethanol and added dropwise at room temperature. The suspension is stirred at room temperature for 1 hour, then filtered off with suction, and the residue is washed three times with 830 ml each time of ethanol. The drying is effected at 50° C. under reduced pressure with supply of air. 1129.6 g of the title compound in the polymorph II are obtained.

Workup

  1. additionadded dropwise at room temperature
  2. filtrationfiltered off with suction
  3. washthe residue is washed three times with 830 ml each time of ethanol
  4. customis effected at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-c968c0b3de584495a5d0a7769e6e977e
Source dataset
uspto-grants-2014_11
Patent number
US08877933B2

Linked notes

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