Hydroxyamine hydrochloride → 1-[(5-Chloroindol-2-yl)sulfonyl]-4-[(hydroxyimino)[5-(pyridin-4-yl)pyrimidin-2-yl]methyl]piperazine

HRID 352924Notes

Reaction equation

HRID 352924 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]([C:22]3[N:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)=[CH:24][N:23]=3)=S)[CH2:16][CH2:15]1)(=[O:13])=[O:12])=[CH:5]2.Cl.[NH2:35][OH:36].C([O-])(=O)C.[Na+]>C(O)C.[Hg](Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([S:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20](=[N:35][OH:36])[C:22]3[N:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)=[CH:24][N:23]=3)[CH2:16][CH2:15]1)(=[O:13])=[O:12])=[CH:5]2

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 865920861-[(5-Chloroindol-2-yl)sulfonyl]-4-[[5-(pyridin-4-yl)pyrimidin-2-yl]thiocarbonyl]piperazine

Product 1

HCID 1363764391-[(5-Chloroindol-2-yl)sulfonyl]-4-[(hydroxyimino)[5-(pyridin-4-yl)pyrimidin-2-yl]methyl]piperazine

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 702EthanolSolvent

Procedure

In ethanol (50 ml) was suspended 1-[(5-chloroindol-2-yl)sulfonyl]-4-[[5-(pyridin-4-yl)pyrimidin-2-yl]thiocarbonyl]piperazine (243 mg) at room temperature, followed by the successive addition of hydroxylamine hydrochloride (338 mg), sodium acetate (399 mg) and mercury (II) chloride (132 mg). The resulting mixture was stirred at room temperature for 6 hours. The insoluble matter was filtered off through Celite filtration. The residue was purified by chromatography on a silica gel column (7% methanol—methylene chloride), whereby two fractions were obtained. They were concentrated, respectively, whereby a low-polarity compound (20 mg, colorless powder) and a high-polarity compound (20 mg, colorless powder) were obtained. Low-polarity compound:

Workup

  1. customat room temperature
  2. filtrationThe insoluble matter was filtered off through Celite filtration
  3. customThe residue was purified by chromatography on a silica gel column (7% methanol—methylene chloride)
  4. customwhereby two fractions were obtained
  5. concentrationThey were concentrated
  6. customrespectively, whereby a low-polarity compound (20 mg, colorless powder) and a high-polarity compound (20 mg, colorless powder) were obtained

Sources & evidence

ORD record
ord-fc3a74b8e4e24755ac82eb416493f431
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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