HCID 86598644, compound → HCID 68636404, compound

HRID 500579Notes

Reaction equation

HRID 500579 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([C:10](O)([CH3:12])[CH3:11])[C:7]([NH:14][CH:15]=O)=[C:6]([F:17])[C:5]=1[NH:18][C:19]1[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][C:20]=1[F:26]>CCOC(C)=O>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]2[C:7](=[C:6]([F:17])[C:5]=1[NH:18][C:19]1[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][C:20]=1[F:26])[N:14]=[CH:15][CH:11]=[C:10]2[CH3:12])=[O:27]

Participants

3

Reactant 1

HCID 86598644HCID 86598644, compound

Product 1

HCID 68636404HCID 68636404, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-(4-bromo-2-fluorophenylamino)-3-fluoro-4-formylamino-5-(1-hydroxy-1-methyl-ethyl)-benzoic acid methyl ester (1.00 equiv.) and polyphosphoric acid is stirred at 160° C. for 20 hours. The reaction mixture is cooled to room temperature and diluted with EtOAc. The organic layer is washed with water and brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that is purified by trituration or flash column chromatography to yield the desired product as necessary.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude material that
  7. customis purified by trituration or flash column chromatography

Sources & evidence

ORD record
ord-c72142dcd10a4e0c9648e5c6c596ca4e
Source dataset
uspto-grants-2010_08
Patent number
US07772234B2

Reaction notes

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