Bicyclo[3.2.1]octan-2-one → N-(Bicyclo[3.2.1]oct-2-yl)-N'-(4-methylpyridazino[4,5-b]indolizin-1-yl) 1,2-ethanediamine

HRID 704083

Reaktionsgleichung

Reaktionsgleichung von HRID 704083
[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][C:2]2=O.Cl.[CH3:11][C:12]1[C:24]2[N:23]3[C:18]([CH:19]=[CH:20][CH:21]=[CH:22]3)=[CH:17][C:16]=2[C:15]([NH:25][CH2:26][CH2:27][NH2:28])=[N:14][N:13]=1>CO.CO.CS(C)=O>[CH:1]12[CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH:2]2[NH:28][CH2:27][CH2:26][NH:25][C:15]1[C:16]2[CH:17]=[C:18]3[N:23]([C:24]=2[C:12]([CH3:11])=[N:13][N:14]=1)[CH:22]=[CH:21][CH:20]=[CH:19]3

Komponenten

5

Edukt 2

HCID 107363Bicyclo[3.2.1]octan-2-oneHCID 20075511HCID 20075511, Verbindung

Produkt 1

HCID 20075513N-(Bicyclo[3.2.1]oct-2-yl)-N'-(4-methylpyridazino[4,5-b]indolizin-1-yl) 1,2-ethanediamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 22036561Dimethyl sulfoxide methanolLösungsmittel

Versuchsvorschrift

Following the procedure of Example 12, bicyclo[3.2.1]octan-2-one in methanol (3 to 4 mL) was added to a solution of N-(4-methylpyridazino[4,5-b]indolizin-1-yl)-1,2-ethanediamine hydrochloride in methanol/DMSO (90 mL:30 mL) which had been heated to boiling and then allowed to cool. After stirring at room temperature overnight, the title compound was obtained as the free base after column chromatography (silica gel, 4:1 methylene chloride:methanol to 100% methanol containing ammonium hydroxide) and recrystallized from isopropyl ether. The compound was converted to the dihydrochloride salt by ethanolic HCl, mp 339°-344° C.

Aufarbeitung

  1. temperaturehad been heated
  2. temperatureto cool

Quellen und Nachweise

ORD-Eintrag
ord-af0ce9f90e2948de88d97fd7b1f2795a
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04985560

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