m-Chloroperbenzoic acid → HCID 59540743, compound

HRID 1677509Notes

Reaction equation

HRID 1677509 reaction equation
[CH3:1][C:2]([CH3:35])([CH3:34])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N:20]4[CH2:25][CH2:24][S:23][CH2:22][CH2:21]4)[CH:15]=3)[N:12]=2)[N:7](COCC[Si](C)(C)C)[CH:6]=1)=[O:4].ClC1C=CC=C(C(OO)=[O:44])C=1>ClCCl>[CH3:1][C:2]([CH3:35])([CH3:34])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N:20]4[CH2:25][CH2:24][S:23](=[O:44])[CH2:22][CH2:21]4)[CH:15]=3)[N:12]=2)[NH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59540649HCID 59540649, compound

Product 1

HCID 59540743HCID 59540743, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a flask was added 2,2-Dimethyl-1-[2-(3-thiomorpholin-4-yl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one (prepared using general procedures described in these Examples) 0.030 gm (0.059 mM), 3-chloroperbenzoic acid (77%) 0.015 gm (0.067 mM), dichloromethane, stirred over night, rinsed with saturated aqueous sodium bicarbonate and purified on preparative TLC plate (3:1 ethyl acetate/hexane) tog give 0.019 gm (0.036 mM, 61% yield) of the sulfoxide. The SEM protecting group was removed following general procedures as described in these Examples to give 2,2-Dimethyl-1-{2-[3-(1-oxo-1lambda*4*-thiomorpholin-4-yl)-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl}-propan-1-one, 0.0025 gm, (0.006 mM) M+1 397.

Workup

  1. customprepared
  2. washrinsed with saturated aqueous sodium bicarbonate
  3. custompurified on preparative TLC plate (3:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b561df96243e40c598728b8f43f21996
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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