HCID 86643928, compound → HCID 59436175, compound

HRID 1895105Notes

Reaction equation

HRID 1895105 reaction equation
[CH3:1][Mg+].[Br-].[F:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14](=[O:19])[C:13]([C:20](N(OC)C)=[O:21])=[N:12]1>C1COCC1>[C:20]([C:13]1[C:14](=[O:19])[C:15]([O:17][CH3:18])=[CH:16][N:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[F:4])[N:12]=1)(=[O:21])[CH3:1]

Participants

4

Reactant 2

HCID 86643928HCID 86643928, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 59436175HCID 59436175, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

MeMgBr (1 M solution in THF, 30 mL, 30 mmol) was added dropwise at −78° C. to a solution of 1-(2-fluorophenyl)-N,5-dimethoxy-N-methyl-4-oxo-1,4-dihydropyridazine-3-carboxamide (3.20 g, 10.4 mmol) in THF (30 mL). After stirring for 1 h, the reaction mixture was quenched with 1 M HCl aqueous solution, saturated with NaCl, and extracted with AcOEt rive times. The combined extracts were dried over MgSO4, and concentrated under reduced pressure. The residue was recrystallized from AcOEt to give the title compound (2.32 g, 85% yield) as pale yellow crystals: mp 154-156° C.; 1H NMR (300 MHz, CDCl3): δ ppm 2.69 (3H, s), 3.91 (3H, s), 7.27-7.38 (2H, m), 7.45-7.53 (1H, m), 7.65 (1H, dt, J=1.5, 7.9 Hz), 7.77 (1H, d, J=2.3 Hz). Anal. Calcd for C13H11FN2O3: C, 59.54; H, 4.23; N, 10.68. Found: C, 59.62; H, 4.22; N, 10.79.

Workup

  1. customthe reaction mixture was quenched with 1 M HCl aqueous solution, saturated with NaCl
  2. extractionextracted with AcOEt rive times
  3. dry with materialThe combined extracts were dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from AcOEt

Sources & evidence

ORD record
ord-7a60753a332647b2a12e502cf413de39
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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