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

HRID 1392941
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1392941
CO[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][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][CH2:11]2)=[N:7][CH:6]=1)=[O:4].Cl.[NH2:31][OH:32].C[O-].[Na+].CO.Cl>O1CCOCC1>[OH:32][NH:31][C:3]([C:5]1[S:9][C:8]([N:10]2[CH2:11][CH2:12][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=3)(=[O:17])=[O:18])[CH2:14][CH2:15]2)=[N:7][CH:6]=1)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 691992162-[4-(4-Trifluoromethoxy-benzene sulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid methyl ester

Produkt 1

HCID 11236322
2-[4-(4-Trifluoromethoxy-benzene sulfonyl)-piperazin-1-yl]-thiazole-5-carboxylic acid hydroxyamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of compound (12d) (125 mg, 0.276 mmol) in 1,4-dioxane (2 mL) were added hydroxylamine hydrochloride (191 mg, 2.76 mmol) and a freshly prepared solution of sodium methoxide in methanol (95 mg, 4.14 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 13d as a solid. HPLC: =92% (Rt=14.16 min).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a0d2ec86bbe94a1a884a3bdcc76c2435
Quelldatensatz
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07345043B2

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