Hydrochloric Acid → tert-butyl 2-[[[(3-furyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamate

HRID 1821842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1821842
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([C:8]2[NH:16][C:11]3=[CH:12][N:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)=O)=[CH:2]1.[C:17]([O:21][C:22](=[O:28])[NH:23][CH2:24][CH2:25][O:26][NH2:27])([CH3:20])([CH3:19])[CH3:18].Cl>C(O)C>[O:1]1[CH:5]=[CH:4][C:3]([C:6](=[N:27][O:26][CH2:25][CH2:24][NH:23][C:22](=[O:28])[O:21][C:17]([CH3:19])([CH3:18])[CH3:20])[C:8]2[NH:16][C:11]3=[CH:12][N:13]=[CH:14][CH:15]=[C:10]3[CH:9]=2)=[CH:2]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 15610443tert-butyl N-(2-(aminooxy)ethyl)carbamateHCID 578934443-Furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone

Produkt 1

HCID 136365984tert-butyl 2-[[[(3-furyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3-Furyl(1H-pyrrolo[2,3-c]pyridin-2-yl)methanone (Example 137) (63 mg, 0.30 mmol) and tert-butyl[2-(aminooxy)ethyl]carbamate (55 mg, 0.31 mmol) were combined in ethanol (5 mL). The pH of the mixture was adjusted to ca. 4 using 1 M ethereal hydrogen chloride and the reaction mixture was refluxed for 12 h. The solvent was removed under vacuum. The residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate solution and then brine, dried over sodium sulfate, and concentrated to a solid. Purification by Biotage chromatography (silica gel, 2 to 18% methanol in dichloromethane) produced tert-butyl 2-[[[(3-furyl)(1H-pyrrolo[2,3-c]pyridin-2-yl)methylene]amino]oxy]ethylcarbamate (50 mg, 45%) as a yellow solid.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 12 h
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution
  5. dry with materialbrine, dried over sodium sulfate
  6. concentrationconcentrated to a solid
  7. customPurification by Biotage chromatography (silica gel, 2 to 18% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-9be96bf9de3a4879866258c2ebf5ff02
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07608627B2

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