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

HRID 1667961Notes

Reaction equation

HRID 1667961 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.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24]>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:23](=[O:24])[C:22]3[CH:26]=[CH:27][CH:28]=[C:20]([C:19]([F:18])([F:29])[F:30])[CH:21]=3)[CH:15]=[CH:16][CH:17]=1)=[N:5]2

Participants

5

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 574410563-(Imidazo[1,2-b]pyridazin-6-yloxy)aniline

Product 1

HCID 57505528N-[3-(imidazo[1,2-b]pyridazin-6-yloxy)phenyl]-3-(trifluoromethyl)benzamideYield 98%

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 3-(trifluoromethyl)benzoyl chloride (0.151 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 diisopropyl ether to give the title compound (195 mg, 98%) 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 diisopropyl ether

Sources & evidence

ORD record
ord-1baf781a7e614bbaa874f9a7341ed223
Source dataset
uspto-grants-2011_10
Patent number
US08044049B2

Reaction notes

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