m-Chloroperbenzoic acid → 2-Isopropyl-7-(2-methanesulfinyl-ethoxy)-4-(5-methyl-1H-pyrazol-3-ylamino)-2H-phthalazin-1-one

HRID 1783713Notes

Reaction equation

HRID 1783713 reaction equation
[CH:1]([N:4]1[N:13]=[C:12]([NH:14][C:15]2[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=2)[C:11]2[C:6](=[CH:7][C:8]([O:21][CH2:22][CH2:23][S:24][CH3:25])=[CH:9][CH:10]=2)[C:5]1=[O:26])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:32]>C(Cl)Cl>[CH:1]([N:4]1[N:13]=[C:12]([NH:14][C:15]2[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=2)[C:11]2[C:6](=[CH:7][C:8]([O:21][CH2:22][CH2:23][S:24]([CH3:25])=[O:32])=[CH:9][CH:10]=2)[C:5]1=[O:26])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 247534922-Isopropyl-4-(5-methyl-1H-pyrazol-3-ylamino)-7-(2-methylsulfanyl-ethoxy)-2H-phthalazin-1-one

Product 1

HCID 247535912-Isopropyl-7-(2-methanesulfinyl-ethoxy)-4-(5-methyl-1H-pyrazol-3-ylamino)-2H-phthalazin-1-oneYield 16.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-isopropyl-4-(5-methyl-1H-pyrazol-3-ylamino)-7-(2-methylsulfanyl-ethoxy)-2H-phthalazin-1-one (0.077 g, 0.23 mmol) in DCM (2 ml), was added m-chloro-peroxybenzoic acid (0.040 g, 0.23 mmol) portion wise. The solution was stirred at RT for 1 hour. After this time LC-MS indicated complete consumption of starting material and the solvent was removed under vacuum. Preparative thin layer chromatography (elution: 50% EtOAc, 50% EtOH) afforded the title compound (0.015 g, 14% yield) as a pale yellow solid.

Workup

  1. customconsumption of starting material
  2. customthe solvent was removed under vacuum
  3. washPreparative thin layer chromatography (elution: 50% EtOAc, 50% EtOH)

Sources & evidence

ORD record
ord-ced49b7e30a54950abb6c681fcae2c93
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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