N,4-dimethoxy-N-methyl-6-oxo-[3-(trifluoromethyl)phenyl]-1,6-dihydropyridazine-3-carboxamide → 6-Acetyl-5-methoxy-2-[3-(trifluoromethyl)phenyl]pyridazin-3(2H)-one

HRID 2089786Notes

Reaction equation

HRID 2089786 reaction equation
[CH3:1][Mg+].[Br-].CON(C)[C:7]([C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12](=[O:17])[N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[N:10]=1)=[O:8]>C1COCC1>[C:7]([C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12](=[O:17])[N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=2)[N:10]=1)(=[O:8])[CH3:1]

Participants

4

Reactant 2

HCID 86643932N,4-dimethoxy-N-methyl-6-oxo-[3-(trifluoromethyl)phenyl]-1,6-dihydropyridazine-3-carboxamideHCID 178418689HCID 178418689, compound

Product 1

HCID 594361466-Acetyl-5-methoxy-2-[3-(trifluoromethyl)phenyl]pyridazin-3(2H)-oneYield 45.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

MeMgBr (1 M solution in THF, 4 mL, 12 mmol) was added dropwise at −78° C. to a solution of N,4-dimethoxy-N-methyl-6-oxo-1-[3-(trifluoromethyl)phenyl]-1,6-dihydropyridazine-3-carboxamide (1.43 g, 4 mmol) in THF (15 mL). After stirring for 1 h, the reaction mixture was quenched with saturated NH4Cl aqueous solution and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with hexane/AcOEt (1/1) and recrystallized from hexane/AcOEt to give the title compound (566 mg, 45% yield) as a white solid: mp 136-138° C.; NMR (300 MHz, CDCl3): δ ppm 2.57 (3H, s), 3.93 (3H, s), 6.31 (1H, s), 7.63 (1H, t, J=7.9 Hz), 7.69 (1H, d, J=7.9 Hz), 7.84-7.88 (1H, m), 7.91 (1H, s). Anal. Calcd for C14H11F3N2O3: C, 53.85; H, 3.55; N, 8.97. Found: C, 53.96; H, 3.57; N, 8.96.

Workup

  1. customthe reaction mixture was quenched with saturated NH4Cl aqueous solution
  2. extractionextracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with hexane/AcOEt (1/1)
  8. customrecrystallized from hexane/AcOEt

Sources & evidence

ORD record
ord-80324d3a62e24d85861608b6bbe6a7fb
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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