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Hydrochloric Acid → 2-[4-(3,4-Dimethoxy-benzene sulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid hydroxyamide

HRID 1392939
Notes
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Reaction equation

HRID 1392939 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=O.Cl.[NH2:30][OH:31].C[O-].[Na+].CO.Cl>O1CCOCC1>[OH:31][NH:30][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 600321252-[4-(3,4-Dimethoxybenzene sulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid methyl ester

Product 1

HCID 11373732
2-[4-(3,4-Dimethoxy-benzene sulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid hydroxyamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of compound (12b) (125 mg, 0.292 mmol) in 1,4-dioxane (2 mL) were added hydroxylamine hydrochloride (202 mg, 2.92 mmol) and a freshly prepared solution of sodium methoxide in methanol (100 mg, 4.35 mmol of sodium dissolved in 1 mL of methanol) under N2 atmosphere. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was acidified to pH˜6 with 1M HCl and the formed precipitates were filtered off. The filtrate was diluted with ethylacetate (5 mL) and water (2 mL) and the organic layer was separated. The aqueous layer was washed with ethyl acetate (5 mL) and the combined organic layers were dried on sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC to give 13b as a solid. HPLC: 86.09% (Rt=12.51 min).

Workup

  1. customthe formed precipitates
  2. filtrationwere filtered off
  3. additionThe filtrate was diluted with ethylacetate (5 mL) and water (2 mL)
  4. customthe organic layer was separated
  5. washThe aqueous layer was washed with ethyl acetate (5 mL)
  6. customthe combined organic layers were dried on sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6c430574cf174151ba4f0e7e40ebd00c
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07345043B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes