Dimethylamine → Dimethyl-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-amine

HRID 548839Notes

Reaction equation

HRID 548839 reaction equation
I[C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1.[CH3:22][NH:23][CH3:24]>[Cu]Br>[CH3:22][N:23]([CH3:24])[C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 866308943-Iodo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine

Product 1

HCID 42630375Dimethyl-[6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazin-3-yl]-amineYield 8%

Reagents, catalysts & solvents 1

HCID 24593copper(I) bromideCatalyst

Procedure

3-Iodo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine (500 mg, 1.3 mmol) was dissolved in an ethanolic solution of dimethylamine (7.5 mL of a 33% solution, excess). After addition of copper(I) bromide (219 mg, 1.5 mmol) the mixture was stirred for 72 h at room temperature followed by heating to 50° C. for 3 h. Then the solvent was evaporated and the residue was stirred with ethyl acetate and saturated aqueous Seignette salt solution. The organic phase was dried with sodium sulfate and evaporated. Chromatography (SiO2, heptane/ethyl acetate=100:0 to 10:90) afforded the title compound as a light yellow oil (30 mg, 8%). MS: m/e=311.1 [M+H]+.

Workup

  1. temperatureby heating to 50° C. for 3 h
  2. customThen the solvent was evaporated
  3. stirringthe residue was stirred with ethyl acetate and saturated aqueous Seignette salt solution
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-ab5bad929f38450eaee156eb48bfcd5a
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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