4-Chloro-3-(trifluoromethyl)aniline → Sorafenib

HRID 2094782Notes

Reaction equation

HRID 2094782 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[O-])=[CH:14][CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].[F:22][C:23]([F:33])([F:32])[C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[Cl:31])[NH2:27]>C(#N)C>[Cl:31][C:30]1[CH:29]=[CH:28][C:26]([NH:27][C:19](=[O:21])[NH:18][C:15]2[CH:14]=[CH:13][C:12]([O:11][C:9]3[CH:8]=[CH:7][N:6]=[C:5]([C:3]([NH:2][CH3:1])=[O:4])[CH:10]=3)=[CH:17][CH:16]=2)=[CH:25][C:24]=1[C:23]([F:22])([F:32])[F:33]

Participants

4

Reactant 2

HCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 86648443HCID 86648443, compound

Product 1

HCID 216239SorafenibYield 87.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-(2-(methylcarbamoyl)pyridin-4-yloxy)phenylcarbamate (25 g, 0.06871 mol) and 3-trifluoromethyl-4-chloroaniline (13.4 g, 0.06871 mol) in acetonitrile (250 ml) was refluxed for 24 hours when product precipitated out of reaction mass. The reaction mass was cooled to room temperature and obtained product was filtered, washed with acetonitrile till a clear filtrate was obtained. It was then vacuum dried to obtain 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)ureido)phenoxy)-N-methylpicolinamide (sorafenib base) (28 g).

Workup

  1. temperaturewas refluxed for 24 hours when product
  2. customprecipitated out of reaction mass
  3. customobtained product
  4. filtrationwas filtered
  5. washwashed with acetonitrile till a clear filtrate
  6. customwas obtained
  7. customvacuum dried

Sources & evidence

ORD record
ord-419518d3a14c419fa09de83b85e545e5
Source dataset
uspto-grants-2013_05
Patent number
US08445687B2

Reaction notes

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