m-Chloroperbenzoic acid → HCID 87626932, compound

HRID 509722Notes

Reaction equation

HRID 509722 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[N:20][CH:19]=3)[C:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][C:10]=3[C:4]=2[CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:33])C=1>ClCCl>[CH3:15][N+:12]1([O-:33])[CH2:13][CH2:14][C:9]2[N:8]([CH2:16][CH2:17][C:18]3[CH:19]=[N:20][C:21]([CH3:24])=[CH:22][CH:23]=3)[C:5]3[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=3[C:10]=2[CH2:11]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 197033Latrepirdine

Product 1

HCID 87626932HCID 87626932, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimebon (500 mg) was dissolved in 10 mL dichloromethane. To this was added a solution of mCPBA (65%, 536 mg) in 5 mL dichloromethane drop wise at 25 deg C. The reaction mixture was stirred at 25 deg C. for 24 h at which point it was found complete (by TLC and LCMS). The solvent was removed under reduced pressure (below 30 deg C.) and the residue was purified by column chromatography on neutral alumina eluting with methanol-dichloromethane gradient to obtain 220 mg of product as light brown oil. TLC Rf 0.5 in 5% MeOH-DCM. This compound also exhibited the following inhibition profile:

Workup

  1. customThe solvent was removed under reduced pressure (below 30 deg C.)
  2. customthe residue was purified by column chromatography on neutral alumina eluting with methanol-dichloromethane gradient

Sources & evidence

ORD record
ord-193de76b35074cb3b3df80d6519ae20d
Source dataset
uspto-grants-2015_08
Patent number
US09096591B2

Reaction notes

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