Ethanolamine → (S)-N-(2-hydroxyethyl)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarboxamide

HRID 539006Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539006
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[CH:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[O:29][C:28](=[O:30])[NH:27][N:26]=4)=[CH:21][CH:20]=3)=[C:12]2[N:11]=1)([CH3:3])[CH3:2].[NH2:31][CH2:32][CH2:33][OH:34]>CCO>[OH:34][CH2:33][CH2:32][NH:31][C:28]([NH:27][NH:26][C:25](=[O:29])[C:22]1[CH:21]=[CH:20][C:19]([C:18]2[CH:17]=[N:16][N:13]3[CH:14]=[CH:15][C:10]([N:5]4[C@@H:4]([CH:1]([CH3:2])[CH3:3])[CH2:8][O:7][C:6]4=[O:9])=[N:11][C:12]=23)=[CH:24][CH:23]=1)=[O:30]

Komponenten

4

Edukt 2

HCID 700EthanolamineHCID 67034488(S)-5-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1,3,4-oxadiazol-2(3H)-one

Produkt 1

HCID 67033962(S)-N-(2-hydroxyethyl)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarboxamideAusbeute 29,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of (S)-5-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1,3,4-oxadiazol-2(3H)-one (42.8 mg, 0.105 mmol) and 2-aminoethanol (19.1 μL, 0.316 mmol) in EtOH (2 mL) was heated to reflux for 22 hours. After the reaction mixture was cooled to ambient temperature, the solvent was removed under reduced pressure. The crude product was flash chromatographed (0-10% MeOH in dichloromethane) to afford 14.4 mg (29%) of (S)—N-(2-hydroxyethyl)-2-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzoyl)hydrazinecarboxamide. LCMS (APCI−) m/z 466.5 [M−H]+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 22 hours
  3. customthe solvent was removed under reduced pressure
  4. customchromatographed (0-10% MeOH in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-d1641a266f3a4f98bb0a19edabfa3b6b
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865726B2

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