HCID 59436282, compound → HCID 59436279, compound

HRID 1895099Notes

Reaction equation

HRID 1895099 reaction equation
CON(C)[C:4]([C:6]1[C:11](=[O:12])[C:10]([CH3:13])=[CH:9][N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[N:7]=1)=[O:5].[CH3:25][Mg]Br>C1COCC1>[C:4]([C:6]1[C:11](=[O:12])[C:10]([CH3:13])=[CH:9][N:8]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)[N:7]=1)(=[O:5])[CH3:25]

Participants

4

Reactant 2

HCID 59436282HCID 59436282, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59436279HCID 59436279, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N,5-dimethyl-4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxamide (0.535 g, 1.6 mmol) in THF (10 mL) at −78° C. was added methylmagnesium bromide (1.1 mL, 3.2 mmol, 3 M in diethyl ether). The reaction was stirred at that temperature for 1 h then quenched with saturated ammonium chloride aqueous solution (5 mL) then water (2 mL) with slow warming to room temperature. The reaction mixture was diluted with ethyl acetate (20 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (2×10 mL) and the combined organic extracts are washed with 1 N HCl aqueous solution (15 mL), brine (15 mL), dried (Na2SO4), filtered and concentrated to provide 3-acetyl-5-methyl-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (0.463 g, 98%) as a light yellow solid.

Workup

  1. customthen quenched with saturated ammonium chloride aqueous solution (5 mL)
  2. additionThe reaction mixture was diluted with ethyl acetate (20 mL)
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×10 mL)
  5. washthe combined organic extracts are washed with 1 N HCl aqueous solution (15 mL), brine (15 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-78fbfde34c4146dd9eb876d8a2df84b2
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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