1,4-Dioxane hydrochloride → N-(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl)hydrazinecarboxamide trihydrochloride

HRID 1465480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1465480
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]3[CH:36]=[CH:35][C:21]([CH2:22][NH:23][C:24]([NH:26][NH:27]C(OC(C)(C)C)=O)=[O:25])=[CH:20][CH:19]=3)=[N:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].O1CCOCC1.[ClH:43]>O1CCOCC1>[ClH:43].[ClH:43].[ClH:43].[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][C:18]3[CH:36]=[CH:35][C:21]([CH2:22][NH:23][C:24]([NH:26][NH2:27])=[O:25])=[CH:20][CH:19]=3)=[N:14][CH:15]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 204431481,4-Dioxane hydrochlorideHCID 58181223Tert-butyl 2-[(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl)carbamoyl]hydrazinecarboxylate

Produkt 1

HCID 67266593N-(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl)hydrazinecarboxamide trihydrochlorideAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of tert-butyl 2-[(4-{2-[5-(4-acetylpiperazin-1-yl)pyridin-2-yl]ethyl}benzyl)carbamoyl]hydrazinecarboxylate (121.0 mg, 0.243 mmol) in anhydrous dioxane (1.2 ml) was added 4M hydrogen chloride dioxane solution (1.2 ml). After stirring at room temperature for 5 hrs, the reaction mixture was concentrated under reduced pressure. Ethyl acetate (10 ml) was added to the residue, and the mixture was concentrated again under reduced pressure. This operation was performed 3 times to azeotropically remove hydrogen chloride gas. The residue was suspended in a mixture of ethanol (3 ml) and ethyl acetate (6 ml), filtered, washed with ethyl acetate and dried under reduced pressure to give the title compound (111.0 mg, yield 90.1%) as a slightly yellow solid.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate (10 ml) was added to the residue
  3. concentrationthe mixture was concentrated again under reduced pressure
  4. additionThe residue was suspended in a mixture of ethanol (3 ml) and ethyl acetate (6 ml)
  5. filtrationfiltered
  6. washwashed with ethyl acetate
  7. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9309e39ea29346b19d937a61290bc583
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999989B2

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