p-Fluorotoluene-alpha-thiol → HCID 59168197, compound

HRID 1444051Notes

Reaction equation

HRID 1444051 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.[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][SH:38])=[CH:33][CH:32]=1>>[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[C:4]([O:28][CH3:29])=[N:3][C:2]([S:38][CH2:37][C:34]2[CH:35]=[CH:36][C:31]([F:30])=[CH:32][CH:33]=2)=[CH:7][N:6]=1)(=[O:10])=[O:11]

Participants

3

Reactant 2

HCID 85171p-Fluorotoluene-alpha-thiolHCID 59168156N-(5-Bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide

Product 1

HCID 59168197HCID 59168197, compound

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 (4-fluorophenyl)methanethiol (0.13 g). The intermediate product containing the SEM group was purified by silica gel chromatography eluting with ethyl acetate/iso-hexane mixtures. Deprotection as for Example 101b gave the title compound. Yield 0.2 g

Workup

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

Sources & evidence

ORD record
ord-3832faf04a6e40abb797a5842e6d9ebf
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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