Chloroacetaldehyde → 7-(4-Bromo-2-fluorophenylamino)-imidazo[1,2-b]pyridazine-6-carboxylic acid

HRID 1161817Notes

Reaction equation

HRID 1161817 reaction equation
C([O:5][C:6]([C:8]1[C:13]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[F:22])=[CH:12][C:11]([NH2:24])(Cl)[NH:10][N:9]=1)=[O:7])(C)(C)C.Cl[CH2:26][CH:27]=O>C(O)C>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:13]2[C:8]([C:6]([OH:5])=[O:7])=[N:9][N:10]3[CH:26]=[CH:27][N:24]=[C:11]3[CH:12]=2)=[C:16]([F:22])[CH:17]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 66998716HCID 66998716, compound

Product 1

HCID 595193857-(4-Bromo-2-fluorophenylamino)-imidazo[1,2-b]pyridazine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspended solution of 6-amino-4-(4-bromo-2-fluoro-phenylamino)-6-chloro-pyridazine-3-carboxylic acid tert-butyl ester (61 mg, 0.16 mmol) in ethanol (5 ml) in a bomb reactor is added at room temperature chloroacetaldehyde (0.12 ml of 50% aqueous solution, 5.0 equivalents). The reaction mixture is sealed and stirred at 80° C. for two days, and then cooled to room temperature. The solvent is removed, and the residue is diluted with ethyl acetate (20 ml). The organic layer is washed with saturated NaCl (20 ml×3), dried over Na2SO4, and concentrated. The residue is purified by flash column chromatography to provide the desired product.

Workup

  1. customThe reaction mixture is sealed
  2. temperaturecooled to room temperature
  3. customThe solvent is removed
  4. additionthe residue is diluted with ethyl acetate (20 ml)
  5. washThe organic layer is washed with saturated NaCl (20 ml×3)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-4597825552e54e20b97f34d156f0dfc4
Source dataset
uspto-grants-2010_10
Patent number
US07820664B2

Reaction notes

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