HCID 86643933, compound → HCID 59436162, compound

HRID 1895151Notes

Reaction equation

HRID 1895151 reaction equation
[F:1][C:2]1([F:26])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH:16]=[C:15]([O:17][CH3:18])[C:14](=[O:19])[C:13]([C:20](N(OC)C)=[O:21])=[N:12]3)[C:4]=2[O:3]1.[CH3:27][Mg+].[Br-]>C1COCC1>[C:20]([C:13]1[C:14](=[O:19])[C:15]([O:17][CH3:18])=[CH:16][N:11]([C:10]2[C:4]3[O:3][C:2]([F:26])([F:1])[O:6][C:5]=3[CH:7]=[CH:8][CH:9]=2)[N:12]=1)(=[O:21])[CH3:27]

Participants

4

Reactant 2

HCID 86643933HCID 86643933, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 59436162HCID 59436162, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-(2,2-difluoro-1,3-benzodioxol-4-yl)-N,5-dimethoxy-N-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamide (2.7 g, 7.2 mmol) in THF (70 mL) was added dropwise 1 M MeMgBr in THF (14 mL, 14 mmol) at −78° C. for 15 min. After stirring at −78° C. for 1 h, the mixture was quenched with 1 M HCl aqueous solution (30 mL). The mixture was warmed to room temperature and extracted with AcOEt. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound (2.3 g, 99% yield) as yellow crystals: 1H NMR (300 MHz, CDCl3): δ ppm 2.69 (3H, s), 3.95 (3H, s), 7.17 (1H, dd, J=7.9, 1.1 Hz), 7.26-7.32 (1H, m), 7.55 (1H, dd, J=8.7, 1.1 Hz), 8.00 (1H, s).

Workup

  1. customthe mixture was quenched with 1 M HCl aqueous solution (30 mL)
  2. temperatureThe mixture was warmed to room temperature
  3. extractionextracted with AcOEt
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-26eab59139784dd0a25460c0b03f2742
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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