6-Amino-3-chloropyridazine → 6-Chloro-2-phenyl-3-pyrid-4-ylimidazo[1,2-b]pyridazine

HRID 80735

Reaction equation

HRID 80735 reaction equation
Br[CH:2]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[Cl:17][C:18]1[N:23]=[N:22][C:21]([NH2:24])=[CH:20][CH:19]=1>C(O)C>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[N:22]([C:2]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:24]=2)[N:23]=1

Participants

4

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 134660102-Bromo-1-phenyl-2-pyrid-4-ylethanone

Product 1

HCID 594069546-Chloro-2-phenyl-3-pyrid-4-ylimidazo[1,2-b]pyridazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 13 g (36.5 mmol) of 2-bromo-1-phenyl-2-pyrid-4-ylethanone (CAS No.: 741633-76-1) and 18.9 g (146 mmol) of 6-chloropyridazin-3-ylamine in 200 mL of ethanol is maintained at 90° C. for 5 hours 30 minutes. After cooling, the solvent is evaporated off under reduced pressure, the medium is taken up in 50 mL of water and the product is extracted with ethyl acetate. The organic phases are dried over magnesium sulfate and then concentrated under reduced pressure.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is evaporated off under reduced pressure
  3. extractionthe product is extracted with ethyl acetate
  4. dry with materialThe organic phases are dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3197f8470dfc43b6a117c10cf499bc10
Source dataset
uspto-grants-2014_09
Patent number
US08846676B2

Linked notes

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