Hydrochloric Acid → 2-[4-(4-Trifluoromethyl-benzenesulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid hydroxyamide

HRID 1392944Notes

Reaction equation

HRID 1392944 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]([C:25]([F:28])([F:27])[F:26])=[CH:21][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[CH2:11][CH2:12][N:13]([S:16]([C:19]3[CH:20]=[CH:21][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:23][CH:24]=3)(=[O:18])=[O:17])[CH2:14][CH2:15]2)=[N:7][CH:6]=1)=[O:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 692010032-[4-(4-Trifluoromethyl-benzenesulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid methyl ester

Product 1

HCID 114873922-[4-(4-Trifluoromethyl-benzenesulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid hydroxyamideYield 16%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of compound 12f (125 mg, 0.287 mmol) in 1,4-dioxane (2 mL) were added hydroxylamine hydrochloride (199 mg, 2.87 mmol) and a freshly prepared solution of sodium methoxide in methanol (99 mg, 4.30 mmol of sodium dissolved in 1 mL of methanol) under a 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 ethyl acetate (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 13f (20 mg, yield 16%). HPLC 85.42% (Rt=14.11 min).

Workup

  1. customthe formed precipitates
  2. filtrationwere filtered off
  3. additionThe filtrate was diluted with ethyl acetate (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-0923a78cb4a84819bcb4b5b38f5b2f5f
Source dataset
uspto-grants-2008_03
Patent number
US07345043B2

Reaction notes

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