Hydroxyamine hydrochloride → But-2-enedioic acid (1-benzenesulfonyl-1H-indol-5-yl)-amide hydroxyamide

HRID 84201

Reaktionsgleichung

Reaktionsgleichung von HRID 84201
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20](Cl)(=[O:26])/[CH:21]=[CH:22]/[C:23](Cl)=[O:24].Cl.[NH2:29][OH:30].C([O-])(O)=O.[Na+]>C1COCC1>[OH:30][NH:29][C:20](=[O:26])[CH:21]=[CH:22][C:23]([NH:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:10]([S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])[CH:11]=[CH:12]2)=[O:24]

Komponenten

6

Edukt 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 5325504Fumaryl chlorideHCID 154501451-(Benzenesulfonyl)-1H-indol-5-amine

Produkt 1

HCID 76035043But-2-enedioic acid (1-benzenesulfonyl-1H-indol-5-yl)-amide hydroxyamideAusbeute 42,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel4×

Versuchsvorschrift

A solution of 27 (0.20 g, 0.73 mmol) in THF (2 mL) was added dropwise to a solution of fumaryl chloride (0.08 mL, 0.73 mmole) in THF (1 mL). The mixture was stirred at room temperature for 10 min and was then dried under vacuum to provide a residue. The residue was then dissolved in THF (mL). In another vessel, to a suspension of hydroxylamine hydrochloride (0.26 g, 3.77 mmole) in THF (4 mL), a sat. NaHCO3 solution (3 ml) was added, and the reaction mixture was stirred at room temperature for 10 min. The contents of both vessels were combined and stirred at room temperature for 1 h. The mixture was partitioned between EtOAc (15 mL×3) and water. The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give a yellow residue, which was purified by silica gel chromatography (CH2Cl2:CH3OH=10:1:1% AcOH) to afford Compound 27 (0.12 g). 1H NMR (500 MHz, CD3OD): δ 7.70 (d, J=3.3 Hz, 1H), 6.86 (d, J=15.0 Hz, 1H), 7.10 (d, J=15.0 Hz, 1H), 7.46-7.51 (m, 3H), 7.58-7.61 (m, 1H), 7.65 (d, J=3.4 Hz, 1H), 7.90-7.97 (m, 4H). HRMS (EI) for C18H15N3O5S (M+): calcd, 385.0732. found, 385.0732.

Aufarbeitung

  1. customwas then dried under vacuum
  2. customto provide a residue
  3. stirringthe reaction mixture was stirred at room temperature for 10 min
  4. stirringstirred at room temperature for 1 h
  5. customThe mixture was partitioned between EtOAc (15 mL×3) and water
  6. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellow residue, which
  9. customwas purified by silica gel chromatography (CH2Cl2:CH3OH=10:1:1% AcOH)

Quellen und Nachweise

ORD-Eintrag
ord-9186ff3bc0c9482eb5f70b01c8a66b39
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846748B2

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