HCID 59436218, compound → HCID 59436274, compound

HRID 1895121Notes

Reaction equation

HRID 1895121 reaction equation
[CH3:1][Mg+].[Br-].CON(C)[C:7]([C:9]1[C:14](=[O:15])[C:13]([CH2:16][O:17][CH3:18])=[CH:12][N:11]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[N:10]=1)=[O:8]>C1COCC1>[C:7]([C:9]1[C:14](=[O:15])[C:13]([CH2:16][O:17][CH3:18])=[CH:12][N:11]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:28])[F:27])[CH:20]=2)[N:10]=1)(=[O:8])[CH3:1]

Participants

4

Reactant 2

HCID 59436218HCID 59436218, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 59436274HCID 59436274, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

MeMgBr (1 M solution in THF, 16 mL, 16 mmol) was added dropwise at −78° C. to a solution of N-methoxy-5-(methoxymethyl)-N-methyl-4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxamide (1.95 g, 5.25 mmol) in THF (50 mL). After stirring for 1 h, the reaction mixture was quenched with saturated NH4Cl aqueous solution and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with AcOEt and recrystallized from hexane/AcOEt to give the title compound (1.42 g, 83% yield) as a pale yellow solid: mp 141-143° C.; 1H NMR (300 MHz, CDCl3): δ ppm 2.68 (3H, s), 3.54 (3H, s), 4.50 (2H, d, J=1.5 Hz), 7.66-7.74 (2H, m), 7.81-7.87 (1H, m), 7.89 (1H, s), 8.38 (1H, t, J=1.5 Hz). Anal. Calcd for C15H13F3N2O3: C, 55.22; H, 4.02; N, 8.59. Found: C, 55.26; H, 3.95; N, 8.58.

Workup

  1. customthe reaction mixture was quenched with saturated NH4Cl aqueous solution
  2. extractionextracted with AcOEt
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with AcOEt
  8. customrecrystallized from hexane/AcOEt

Sources & evidence

ORD record
ord-dd22996bd206442995cdf5cfecc25cde
Source dataset
uspto-grants-2013_08
Patent number
US08513251B2

Reaction notes

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