m-Chloroperbenzoic acid → HCID 22004598, compound

HRID 324372Notes

Reaction equation

HRID 324372 reaction equation
[CH2:1]([N:8]([C:13]1[N:18]=[C:17]([CH3:19])[N:16]=[C:15]2[N:20]([C:25]3[C:30]([Cl:31])=[CH:29][C:28]([Cl:32])=[CH:27][C:26]=3[Cl:33])[N:21]=[C:22]([S:23][CH3:24])[C:14]=12)[CH2:9][CH2:10][CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:42])C=1>C(Cl)Cl>[CH2:1]([N:8]([C:13]1[N:18]=[C:17]([CH3:19])[N:16]=[C:15]2[N:20]([C:25]3[C:30]([Cl:31])=[CH:29][C:28]([Cl:32])=[CH:27][C:26]=3[Cl:33])[N:21]=[C:22]([S:23]([CH3:24])=[O:42])[C:14]=12)[CH2:9][CH2:10][CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22004591HCID 22004591, compound

Product 1

HCID 22004598HCID 22004598, compoundYield 110.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-{benzyl-[6-methyl-3-methylsulfanyl-1-(2,4,6-trichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-amino}propanol (42 mg, 0.077 mmol) and m-chloroperbenzoic acid (14 mg, 0.081 mmol) in 0.5 ml of methylene chloride was stirred at room temperature for 3 hours. The mixture was quenched with water and saturated sodium thiosulfate, and extracted with methylene chloride. The organic layer was washed with saturated sodium bicarbonate, dried and concentrated to give an oil which was purified through silica gel column chromatography using 2% methanol in chloroform as eluent to give 46 mg of the title compound as a white glass form. 1H NMR (CDCl3): 1.88(m,2H), 2.54(s,3H), 2.73(s,3H), 3.5-3.7(m,4H), 4.3(m,1H), 5.15(ABq,JAB=16Hz,2H), 7.2-7.4(m,5H), 8.47(ABq,2H)ppm.

Workup

  1. customThe mixture was quenched with water and saturated sodium thiosulfate
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with saturated sodium bicarbonate
  4. customdried
  5. concentrationconcentrated
  6. customto give an oil which
  7. customwas purified through silica gel column chromatography

Sources & evidence

ORD record
ord-8beb598696e84ee298ccca0f0d785553
Source dataset
uspto-grants-2001_04
Patent number
US06218397B1

Reaction notes

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