HCID 58072406, compound → HCID 58072486, compound

HRID 1805587Notes

Reaction equation

[F:1][C:2]1[C:7]([F:8])=[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][C:3]=1[N:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18](=[O:23])[C:17]([C:24](N(OC)C)=[O:25])=[N:16]1.[CH3:30][Mg+].[Br-]>C1COCC1>[C:24]([C:17]1[C:18](=[O:23])[C:19]([O:21][CH3:22])=[CH:20][N:15]([C:3]2[CH:4]=[CH:5][C:6]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[C:7]([F:8])[C:2]=2[F:1])[N:16]=1)(=[O:25])[CH3:30]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1-(2,3-difluoro-4-morpholin-4-ylphenyl)-N,5-dimethoxy-N-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamide (1.1 g, 2.6 mmol) in THF (25 mL) was added dropwise to MeMgBr (1.0 M in THF, 11 mL, 11 mmol) at −78° C. under N2. The mixture was stirred at −78° C. for 1 h. The reaction was quenched with 1 M HCl aqueous solution (11 mL) at −78° C. The mixture warmed up to room temperature, diluted with AcOEt, and washed with brine. The organic layer was dried over MgSO4, and concentrated under reduced pressure. The residue was recrystallized from iPr2O/AcOEt to give the title compound (870 mg, 92% yield) as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6): δ ppm 2.49 (3H, s), 2.90-3.28 (4H, m), 3.64-4.01 (7H, m), 7.05 (1H, td, J=8.9, 2.3 Hz), 7.53 (1H, td, J=8.6, 2.5 Hz), 8.50 (1H, d, J=1.9 Hz). LC-MS (ESI) m/z 366 [M+H]+.

Workup

customThe reaction was quenched with 1 M HCl aqueous solution (11 mL) at −78° C
temperatureThe mixture warmed up to room temperature
additiondiluted with AcOEt
washwashed with brine
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from iPr2O/AcOEt

Sources & evidence

ORD record: ord-ee47b2a5a6334bc1bce397b1df2db524
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354411B2

Reaction notes

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