HCID 86643928, compound → HCID 59436175, compound

HRID 1407097Notes

Reaction equation

HRID 1407097 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 five 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 five 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-1d801fefdc28474f8188cf3136486f50
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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