HCID 59436141, compound → HCID 59436177, compound

HRID 1805573Notes

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 0.1 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 0.1 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-dd309b13b7d743c1b62b4f50d113984d
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354411B2

Reaction notes

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