Benzoyl chloride → N-[3-(imidazo[1,2-b]pyridazin-6-yloxy)phenyl]benzamide

HRID 2391271Notes

Reaction equation

HRID 2391271 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([O:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14])=[N:5]2.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN1CCCC1=O.[OH-].[Na+]>[N:1]1[CH:2]=[CH:3][N:4]2[C:9]=1[CH:8]=[CH:7][C:6]([O:10][C:11]1[CH:12]=[C:13]([NH:14][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:15]=[CH:16][CH:17]=1)=[N:5]2

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 574410563-(Imidazo[1,2-b]pyridazin-6-yloxy)aniline

Product 1

HCID 57441057N-[3-(imidazo[1,2-b]pyridazin-6-yloxy)phenyl]benzamideYield 74%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-(imidazo[1,2-b]pyridazin-6-yloxy)aniline (113 mg, 0.50 mmol) in N-methylpyrrolidone (1.0 mL) was added benzoyl chloride (0.116 mL, 1.00 mmol), and the mixture was stirred at room temperature for 18 hr. The reaction mixture was diluted with 1N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with 1N aqueous sodium hydroxide solution and saturated brine, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→75/25) and precipitated from ethyl acetate to give the title compound (122 mg, 74%) as a white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 1N aqueous sodium hydroxide solution and saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol=100/0→75/25)
  5. customprecipitated from ethyl acetate

Sources & evidence

ORD record
ord-c34588360c0b449b8ed5ee77749b3bc2
Source dataset
uspto-grants-2012_09
Patent number
US08273741B2

Reaction notes

Loading…