Acetamide, 2-mercapto-N-methyl- → 2-[5-(2,3-Dichlorobenzenesulphonylamino)-6-methoxy-2-pyrazinylsulphanyl]-N-methylacetamide

HRID 1444049Notes

Reaction equation

HRID 1444049 reaction equation
Br[C:2]1[N:3]=[C:4]([O:28][CH3:29])[C:5]([N:8](COCC[Si](C)(C)C)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])(=[O:11])=[O:10])=[N:6][CH:7]=1.[SH:30][CH2:31][C:32]([NH:34][CH3:35])=[O:33]>>[Cl:19][C:13]1[C:14]([Cl:18])=[CH:15][CH:16]=[CH:17][C:12]=1[S:9]([NH:8][C:5]1[N:6]=[CH:7][C:2]([S:30][CH2:31][C:32]([NH:34][CH3:35])=[O:33])=[N:3][C:4]=1[O:28][CH3:29])(=[O:10])=[O:11]

Participants

3

Reactant 2

HCID 4047279Acetamide, 2-mercapto-N-methyl-HCID 59168156N-(5-Bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide

Product 1

HCID 591682072-[5-(2,3-Dichlorobenzenesulphonylamino)-6-methoxy-2-pyrazinylsulphanyl]-N-methylacetamide

Procedure

Prepared as for Example 101b using N-(5-bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide (Example 55a) (0.4 g) and 2-mercapto-N-methylacetamide (0.1 g). The intermediate product containing the SEM (2-[trimethylsilyl]ethoxymethyl) group was purified by silica gel chromatography eluting with ethyl acetate/iso-hexane mixtures. Deprotection as for Example 101b gave the title compound. Yield 0.05 g.

Workup

  1. customPrepared as for Example 101b
  2. additionThe intermediate product containing the SEM (2-[trimethylsilyl]ethoxymethyl) group
  3. customwas purified by silica gel chromatography
  4. washeluting with ethyl acetate/iso-hexane mixtures

Sources & evidence

ORD record
ord-21c492ec1e784cb49b997f99895bb06e
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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