m-Chloroperbenzoic acid → HCID 117601253, compound

HRID 1773695Notes

Reaction equation

HRID 1773695 reaction equation
[CH:1]1([C:4]2[C:9]([C:10]3[C:18]4[NH:17][C:16](=[O:19])[NH:15][C:14]=4[CH:13]=[C:12]([C:20]4[C:21]([CH3:26])=[N:22][O:23][C:24]=4[CH3:25])[CH:11]=3)=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:32]>CO.C(Cl)Cl>[CH:1]1([C:4]2[C:9]([C:10]3[C:18]4[NH:17][C:16](=[O:19])[NH:15][C:14]=4[CH:13]=[C:12]([C:20]4[C:21]([CH3:26])=[N:22][O:23][C:24]=4[CH3:25])[CH:11]=3)=[CH:8][CH:7]=[CH:6][N+:5]=2[O-:32])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86296965HCID 86296965, compound

Product 1

HCID 117601253HCID 117601253, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

4-(2-cyclopropylpyridin-3-yl)-6-(3,5-dimethylisoxazol-4-yl)-1H-benzo[d]imidazol-2(3H)-one (35 mg, 0.1 mmol) was dissolved in MeOH/DCM (1/1 mL). To the solution was added 3-Chloroperoxybenzoic acid (69.75 mg, 0.4 mol) and the mixture stirred at RT overnight. The organic solvent was evaporated and the residue was purified with Prep HPLC (0-100% CH3CN/H2O) to afford 2-cyclopropyl-3-(6-(3,5-dimethylisoxazol-4-yl)-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)pyridine 1-oxide.

Workup

  1. customThe organic solvent was evaporated
  2. customthe residue was purified with Prep HPLC (0-100% CH3CN/H2O)

Sources & evidence

ORD record
ord-835c3ed8a86442b785259f10cd0a0d97
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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