Hydrazine → HCID 68637515, compound

HRID 500574Notes

Reaction equation

HRID 500574 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([F:24])[C:8]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=3[F:23])=[C:9]([C:12]([OH:14])=O)[CH:10]=2)[N:5]=[N:4][CH:3]=1.C1C=CC2N(O)[N:32]=[N:31]C=2C=1.CCN=C=NCCCN(C)C.NN>CN(C=O)C.CCOC(C)=O>[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([F:24])[C:8]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=3[F:23])=[C:9]([C:12]([NH:31][NH2:32])=[O:14])[CH:10]=2)[N:5]=[N:4][CH:3]=1

Participants

7

Reactant 4

HCID 9321HydrazineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 68637795HCID 68637795, compound

Product 1

HCID 68637515HCID 68637515, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-amino-7-(4-bromo-2-fluorophenylamino)-8-fluoro-cinnoline-6-carboxylic acid (1.00 equiv.) and HOBt (3.00 equiv.) in DMF is added EDCI (3.00 equiv.) at room temperature. After stirring for 1 hour, hydrazine (3.00 equiv.) and TEA (3.00 equiv.) are added. The reaction mixture is stirred for 1 hour and diluted with EtOAc. The resulting mixture is washed with saturated aqueous NH4Cl, brine, saturated aqueous NaHCO3, and brine. The organic layer is dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude material that is used directly without further purification.

Workup

  1. stirringThe reaction mixture is stirred for 1 hour
  2. washThe resulting mixture is washed with saturated aqueous NH4Cl, brine, saturated aqueous NaHCO3, and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eda98b5dbd29462782e83650a6593250
Source dataset
uspto-grants-2010_08
Patent number
US07772234B2

Reaction notes

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