5-[(Oxiran-2-yl)methoxy]-3,4-dihydroquinolin-2(1H)-one → 6-[4-[2-[3-(3,4-di hydrocarbostyril-5-yloxy)2-hydroxypropylamino]-2-methyl-propylamino]phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 654076Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 654076
[NH2:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:7][CH:6]=1.[NH:20]1[C:30]2[C:25](=[C:26]([O:31][CH2:32][CH:33]3[O:35][CH2:34]3)[CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23][C:21]1=[O:22]>C(O)(C)C>[NH:20]1[C:30]2[C:25](=[C:26]([O:31][CH2:32][CH:33]([OH:35])[CH2:34][NH:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]3[CH:6]=[CH:7][C:8]([C:11]4[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=4)=[CH:9][CH:10]=3)[CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23][C:21]1=[O:22]

Komponenten

4

Edukt 2

HCID 128994235-[(Oxiran-2-yl)methoxy]-3,4-dihydroquinolin-2(1H)-oneHCID 150205046-[4-(2-amino-2-methylpropylamino)phenyl]-4,5-dihydro-3(2H)-pyridazinone

Produkt 1

HCID 197553136-[4-[2-[3-(3,4-di hydrocarbostyril-5-yloxy)2-hydroxypropylamino]-2-methyl-propylamino]phenyl]-4,5-dihydro-3(2H)-pyridazinoneAusbeute 49,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

3.1 g of 6-[4-(2-amino-2-methylpropylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinone obtained in Example 1, (3) and 2.2 g of 1-(3,4-dihydrocarbostyril-5-yloxy)-2,3-epoxypropane were dissolved in 30 ml of isopropyl alcohol and heated with stirring for 20 hours. After the end of the reaction, the reaction solution was concentrated under reduced pressure. The residue was separated by silica gel chromatography (chloroform-methanol=10:1). Recrystallization from dichloro-methane-isopropanol gave 2.4 g of 6-[4-[2-[3-(3,4-di hydrocarbostyril-5-yloxy)2-hydroxypropylamino]-2-methyl-propylamino]phenyl]-4,5-dihydro-3(2H)-pyridazinone.

Aufarbeitung

  1. temperatureheated
  2. customAfter the end of the reaction
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customThe residue was separated by silica gel chromatography (chloroform-methanol=10:1)
  5. customRecrystallization from dichloro-methane-isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-b2e6686860094904a0ae30aafac771eb
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05130314

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