m-Chloroperbenzoic acid → HCID 18923325, compound

HRID 1290223Notes

Reaction equation

HRID 1290223 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([CH3:34])[C:21](=[O:33])[CH2:22][NH:23][C:24](=[O:32])[CH2:25][N:26]4[CH2:31][CH2:30][S:29][CH2:28][CH2:27]4)[C:14]=3[Cl:35])[C:5]2=[N:4][C:3]=1[CH3:36].ClC1C=CC=C(C(OO)=[O:45])C=1>C(Cl)Cl>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([N:20]([CH3:34])[C:21](=[O:33])[CH2:22][NH:23][C:24](=[O:32])[CH2:25][N:26]4[CH2:27][CH2:28][S:29](=[O:45])[CH2:30][CH2:31]4)[C:14]=3[Cl:35])[C:5]2=[N:4][C:3]=1[CH3:36]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18923290HCID 18923290, compound

Product 1

HCID 18923325HCID 18923325, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-8-[2,6-dichloro-3-[N-methyl-N-[(thiomorpholinoacetyl)glycyl]amino]benzyloxy]-2-methylimidazo[1,2-a]pyridine (200 mg) in methylene chloride (2 ml) was added m-chloroperbenzoic acid (80% purity, 76 mg) under ice-bath cooling, and the mixture was stirred for 1 hour at the same temperature. The reaction mixture was washed with water twice and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography (methylene chloride:methanol=5:1, V/V) to give 3-bromo-8-[2,6-dichloro-3-[N-methyl-N-[[(1-oxothiomorpholino)acetyl]glycyl]amino]benzyloxy]-2-methylimidazo[1,2-a]-pyridine (96 mg) as an amorphous.

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with water twice
  3. dry with materialbrine, dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin layer chromatography (methylene chloride:methanol=5:1, V/V)

Sources & evidence

ORD record
ord-4f371a211d5e4e0c9ba02605081ada72
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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