Acetonitrile → HCID 67139353, compound

HRID 1444010Notes

Reaction equation

HRID 1444010 reaction equation
[Cl:1][C:2]1[C:7](Cl)=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([N:12]([C:21]1[C:26]([O:27][CH2:28][C:29]2C=N[CH:32]=[CH:33][CH:34]=2)=[N:25][C:24](Cl)=[CH:23][N:22]=1)COCC[Si](C)(C)C)(=[O:11])=[O:10].C(=O)([O-])[O-].[Cs+].[Cs+].[ClH:42].[NH2:43][CH2:44][CH2:45][SH:46].C(OCC)(=O)C.[C:53](#[N:55])C>>[NH2:43][CH2:44][CH2:45][S:46][C:24]1[N:25]=[C:26]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:53][N:55]=2)[C:21]([NH:12][S:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([Cl:42])[C:2]=2[Cl:1])(=[O:10])=[O:11])=[N:22][CH:23]=1

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 9082Cysteamine HydrochlorideHCID 10796Cesium carbonateHCID 59168094HCID 59168094, compound

Product 1

HCID 67139353HCID 67139353, compound

Procedure

A mixture of 2,3-dichloro-N-[5-chloro-3-(3-pyridinylmethoxy)-2-pyrazinyl]-N-[2-trimethylsilanylethoxymethyl]benzenesulphonamide (Example 101a) (0.68 g), caesium carbonate (1.9 g) and 2-aminoethanethiol hydrochloride (0.2 g) in acetonitrile (5 mL) was stirred at room temperature for 5 h. Ethyl acetate was added and the mixture washed with water and brine. The organic layer was dried (MgSO4) and evaporated. The residue was dissolved in trifluoracetic acid. After 1 h, toluene was added and the mixture evaporated to dryness. HCl (1M in dioxane) was added and the solid collected by filtration (0.2 g).

Workup

  1. washthe mixture washed with water and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. dissolutionThe residue was dissolved in trifluoracetic acid
  5. waitAfter 1 h
  6. additiontoluene was added
  7. customthe mixture evaporated to dryness
  8. additionHCl (1M in dioxane) was added
  9. filtrationthe solid collected by filtration (0.2 g)

Sources & evidence

ORD record
ord-fc3d50993b0f49a2b046c65be70d0fed
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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