Hydrazine → 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid hydrazide

HRID 2102401Notes

Reaction equation

HRID 2102401 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([F:22])=[C:11]3[N:20]=[CH:19][N:18]([CH3:21])[C:12]3=[N:13][C:14]=2[C:15](O)=[O:16])=[C:4]([F:23])[CH:3]=1.C1C=CC2N(O)[N:31]=[N:30]C=2C=1.CCN=C=NCCCN(C)C.NN>CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([F:22])=[C:11]3[N:20]=[CH:19][N:18]([CH3:21])[C:12]3=[N:13][C:14]=2[C:15]([NH:30][NH2:31])=[O:16])=[C:4]([F:23])[CH:3]=1

Participants

6

Reactant 4

HCID 9321HydrazineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 69006569HCID 69006569, compound

Product 1

HCID 690025666-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid hydrazide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(4-bromo-2-fluorophenylamino)-7-fluoro-3-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid (1.00 equivalent) and HOBt (3.00 equivalents) is added EDCI (3.00 equivalents) at room temperature. After stirring for 1 hour, hydrazine (3.00 equivalents) and TEA (3.00 equivalents) 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 in vacuo 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 in vacuo

Sources & evidence

ORD record
ord-f7ba45bf358048a39d0e3fce0a61aec1
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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