m-Chloroperbenzoic acid → HCID 87626932, compound

HRID 574424Notes

Reaction equation

HRID 574424 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-a04e9d43a8bc47598997725493117cf3
Source dataset
uspto-grants-2015_05
Patent number
US09034880B2

Reaction notes

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