HCID 59436141, compound → HCID 59436177, compound

HRID 1624691Notes

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:16]=[N:17][CH:18]=[CH:19][CH:20]=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]=[N:17][CH:18]=[CH:19][CH:20]=2)[N:7]=1)(=[O:5])[CH3:22]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of N,5-dimethoxy-N-methyl-4-oxo-1-pyridin-3-yl-1,4-dihydropyridazine-3-carboxamide (0.40 g, 1.4 mmol) in THF (10 ml) was added dropwise 1 M MeMgBr in THF (3.0 ml, 3.0 mmol) at −78° C. After stirring at −78° C. for 2 h, the mixture was quenched with water (0.5 ml) and stirred at room temperature for 1 h. The mixture was concentrated under reduced pressure. The residue was partitioned between CHCl3 (25 ml) and brine. The aqueous layer was extracted with CHCl3 (25 ml×3). The combined organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (0.21 g, 62% yield) as yellow crystals: 1H NMR (300 MHz, CDCl3): δ ppm 2.70 (3H, s), 3.97 (3H, s), 7.49-7.56 (1H, m), 7.95 (1H, s), 8.01-8.08 (1H, m), 8.72 (1H, dd, J=4.7, 1.3 Hz), 8.95 (1H, d, J=2.6 Hz).

Workup

customthe mixture was quenched with water (0.5 ml)
stirringstirred at room temperature for 1 h
concentrationThe mixture was concentrated under reduced pressure
customThe residue was partitioned between CHCl3 (25 ml) and brine
extractionThe aqueous layer was extracted with CHCl3 (25 ml×3)
dry with materialThe combined organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-8152acb31ef54b85bb1e77919e1c7d63
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778944B2

Reaction notes

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