m-Chloroperbenzoic acid → HCID 59540903, compound

HRID 1677536Notes

Reaction equation

HRID 1677536 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:16]=[C:17]3[C:23]([C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:22][NH:21][C:18]3=[N:19][CH:20]=2)[CH:6]=[C:7]([N:9]2[CH2:14][CH2:13][S:12][CH2:11][CH2:10]2)[CH:8]=1.C1C=C(Cl)C=C(C(OO)=[O:38])C=1>C(Cl)Cl.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:16]=[C:17]3[C:23]([C:24](=[O:29])[C:25]([CH3:26])([CH3:28])[CH3:27])=[CH:22][NH:21][C:18]3=[N:19][CH:20]=2)[CH:6]=[C:7]([N:9]2[CH2:10][CH2:11][S:12](=[O:38])[CH2:13][CH2:14]2)[CH:8]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59540663HCID 59540663, compound

Product 1

HCID 59540903HCID 59540903, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2-(3-methoxy-5-thiomorpholin-4-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (80 mg, 0.195 mmol) in methylene chloride (5 ml) and methanol (5 drops) was added m-CPBA (44 mg, 0.195 mmol). After 1 hour the crude material was loaded onto 2 preparative TLC plates, eluting with 10% methanol in methylene chloride. The product band was collected to afford 61 mg of 1-{2-[3-methoxy-5-(1-oxo-1lambda*4*-thiomorpholin-4-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-2,2-dimethyl-propan-1-one as a light yellow-brown solid. MP 259-260° C., M+H=427.

Workup

  1. washeluting with 10% methanol in methylene chloride
  2. customThe product band was collected

Sources & evidence

ORD record
ord-db67a000011c47909d8e978194c45a08
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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