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 1588230Notes

Reaction equation

HRID 1588230 reaction equation
[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]

Participants

4

Reactant 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

Product 1

HCID 197553136-[4-[2-[3-(3,4-di hydrocarbostyril-5-yloxy)2-hydroxypropylamino]-2-methyl-propylamino]phenyl]-4,5-dihydro-3(2H)-pyridazinoneYield 49.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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 (chloroformmethanbol=10:1). Recrystallization from dichloromethane -isopropanol gave 2.4 g of 6-[4-[2-[3-(3,4-di hydrocarbostyril-5-yloxy)2-hydroxypropylamino]-2-methylpropylamino]phenyl]-4,5-dihydro-3(2H)-pyridazinone.

Workup

  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 (chloroformmethanbol=10:1)
  5. customRecrystallization from dichloromethane -isopropanol

Sources & evidence

ORD record
ord-93bc956f63a744658211816563882640
Source dataset
uspto-grants-1993_06
Patent number
US05221674

Reaction notes

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