Ammonia → HCID 68637740, compound

HRID 500573Notes

Reaction equation

HRID 500573 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:24])[C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=1[F:23])[N:11]=[N:10][CH:9]=[C:8]2Cl)=[O:4].[NH3:26]>CO.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:24])[C:14]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=1[F:23])[N:11]=[N:10][CH:9]=[C:8]2[NH2:26])=[O:4]

Participants

5

Reactant 2

HCID 222Ammonia2×HCID 68638665HCID 68638665, compound

Product 1

HCID 68637740HCID 68637740, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-(4-bromo-2-fluorophenylamino)-4-chloro-8-fluoro-cinnoline-6-carboxylic acid methyl ester (1.00 equiv.) in saturated NH3 in MeOH is refluxed for 16 hours. Additional saturated NH3 in MeOH is added as the reaction progresses if necessary. The reaction mixture is cooled to room temperature and diluted with EtOAc. The organic layer is washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude product that is purified by trituration or flash column chromatography to afford the desired product as necessary.

Workup

  1. washThe organic layer is washed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product that
  6. customis purified by trituration or flash column chromatography

Sources & evidence

ORD record
ord-c08b72f8a8114b2b88dc6b13a4f27309
Source dataset
uspto-grants-2010_08
Patent number
US07772234B2

Reaction notes

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