m-Chloroperbenzoic acid → HCID 178504620, compound

HRID 1809687Notes

Reaction equation

HRID 1809687 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][NH:26][C:27]2[N:32]=[C:31]3[NH:33][N:34]=[C:35]([C:36]4[CH:41]=[CH:40][N:39]=[C:38]([S:42][CH3:43])[N:37]=4)[C:30]3=[CH:29][N:28]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>ClCCl.CO>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][NH:26][C:27]2[N:32]=[C:31]3[NH:33][N:34]=[C:35]([C:36]4[CH:41]=[CH:40][N:39]=[C:38]([S:42]([CH3:43])=[O:9])[N:37]=4)[C:30]3=[CH:29][N:28]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1785034334-{[3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 178504620HCID 178504620, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

m-CPBA (339 mg, 1.98 mmol) was added slowly to a solution of 4-{[3-(2-methylsulfanyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (from Example 14 supra) (450 mg, 0.99 mmol) in a mixture of dichloromethane and methanol (80 mL, 1:1). The reaction mixture was stirred at room temperature for 20 minutes. The solvent was then removed under reduced pressure and the solid was purified by column chromatography (silica gel, 15 g, 200-300 mesh, eluting with dichloromethane:methanol, 50:1 to 30:1) to afford 4-{[3-(2-methanesulfinyl-pyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester. (Yield 150 mg, 32.3%).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe solid was purified by column chromatography (silica gel, 15 g, 200-300 mesh, eluting with dichloromethane:methanol, 50:1 to 30:1)

Sources & evidence

ORD record
ord-235e434a973a461a8ebe829e42e4d561
Source dataset
uspto-grants-2013_01
Patent number
US08362023B2

Reaction notes

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