HCID 59436187, compound → HCID 59436269, compound

HRID 1895144Notes

Reaction equation

HRID 1895144 reaction equation
CON(C)[C:4]([C:6]1[C:11](=[O:12])[C:10]([O:13][CH3:14])=[CH:9][N:8]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[N:7]=1)=[O:5].[CH3:22][Mg+].[Br-]>C1COCC1>[C:4]([C:6]1[C:11](=[O:12])[C:10]([O:13][CH3:14])=[CH:9][N:8]([C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)[N:7]=1)(=[O:5])[CH3:22]

Participants

4

Reactant 2

HCID 59436187HCID 59436187, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 59436269HCID 59436269, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of N,5-dimethoxy-N-methyl-4-oxo-1-pyridin-4-yl-1,4-dihydropyridazine-3-carboxamide (9.6 g, 33 mmol) in THF (100 mL) was added dropwise 1 M MeMgBr in THF (66 mL, 66 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 (70 mL). The mixture was warmed to room temperature, basified with 1 M NaOH aqueous solution, washed with AcOEt. The aqueous layer was extracted with CH2Cl2 (50 mL×4). The combined extract was dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound (2.1 g, 26% yield) as yellow crystals: 1H NMR (300 MHz, CDCl3): δ ppm 2.70 (3H, s), 3.98 (3H, s), 7.64 (2H, dd, J=4.7, 1.6 Hz), 8.04 (1H, s), 8.79 (2H, dd, J=4.7, 1.6 Hz).

Workup

  1. customthe mixture was quenched with 1 M HCl aqueous solution (70 mL)
  2. temperatureThe mixture was warmed to room temperature
  3. washwashed with AcOEt
  4. extractionThe aqueous layer was extracted with CH2Cl2 (50 mL×4)
  5. extractionThe combined extract
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a47b37d4bfa4b79bb186c7457cf1163
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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