Monoperoxyphthalic Acid Magnesium Salt → HCID 57647124, compound

HRID 1714871Notes

Reaction equation

HRID 1714871 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:25])([F:24])[F:23])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:30].[Mg+2]>C(Cl)Cl.CO.C([O-])(O)=O.[Na+]>[CH3:1][S:2]([C:3]1[N:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]([F:23])([F:25])[F:24])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)=[O:30]

Participants

5

Reactant 2

HCID 10130449Monoperoxyphthalic Acid Magnesium Salt2×HCID 57647142HCID 57647142, compound

Product 1

HCID 57647124HCID 57647124, compound

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 3-(methylthio)-6-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}pyridazine (1.62 g, 4.39 mmol) in CH2Cl2/MeOH (2:1, 22 mL) was added magnesium monoperoxyphthalate (1.3 g, 2.2 mmol). The mixture was stirred at room temperature for 18 h. Additional magnesium monoperoxyphthalate (300 mg) was added and after 1 h, the mixture was diluted with saturated aqueous NaHCO3 (50 mL), extracted with (3×20 mL) of EtOAc and dried over Na2SO4. Evaporation of the solvent followed by purification by Combiflash chromatography (SiO2, eluant 5% MeOH/EtOAc) afforded the desired product. 1H NMR (500 MHz, acetone-d6): δ 1.92-1.98 (m, 2H), 2.14-2.18 (m, 2H), 2.84 (s, 3H), 3.90-4.08 (m, 5H), 5.01-5.03 (m, 1H), 7.11 (t, 1H), 7.38 (d, 1H), 7.51 (d, 1H), 7.61-7.67 (m, 2H), 7.82 (d, 1H). MS (+ESI) m/z 386 (MH+).

Workup

  1. extractionextracted with (3×20 mL) of EtOAc
  2. dry with materialdried over Na2SO4
  3. customEvaporation of the solvent
  4. customfollowed by purification by Combiflash chromatography (SiO2, eluant 5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-f91d4330901d4344a46083496cf08e54
Source dataset
uspto-grants-2010_09
Patent number
US07799787B2

Reaction notes

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