1-(2-Cyano-5-chlorophenoxy)-2,3-epoxypropane → 6-[4-[2-[3-(5-chloro-2-cyanophenoxy)-2-hydroxypropylamino]-2-methylpropylamino]-phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 1090626Notes

Reaction equation

HRID 1090626 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.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:32]#[N:33])=[C:25]([CH:31]=1)[O:26][CH2:27][CH:28]1[O:30][CH2:29]1>C(O)(C)C>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:32]#[N:33])=[C:25]([CH:31]=1)[O:26][CH2:27][CH:28]([OH:30])[CH2:29][NH:1][C:2]([CH3:19])([CH3:18])[CH2:3][NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH2:12][CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 145786801-(2-Cyano-5-chlorophenoxy)-2,3-epoxypropaneHCID 150205046-[4-(2-amino-2-methylpropylamino)phenyl]-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 150205066-[4-[2-[3-(5-chloro-2-cyanophenoxy)-2-hydroxypropylamino]-2-methylpropylamino]-phenyl]-4,5-dihydro-3(2H)-pyridazinoneYield 87.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5.2 g of 6-[4-(2-amino-2-methylpropylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinone obtained in Example 1, (3) and 4.4 g of 1-(5-chloro-2-cyanophenoxy)-2,3-epoxypropane were dissolved in 30 ml of isopropyl alcohol, and the solution was heated with stirring for 20 hours. The solution was then worked up as in Example 1, (5) to give 8.2 g of 6-[4-[2-[3-(5-chloro-2-cyanophenoxy)-2-hydroxypropylamino]-2-methylpropylamino]-phenyl]-4,5-dihydro-3(2H)-pyridazinone.

Workup

  1. temperaturethe solution was heated

Sources & evidence

ORD record
ord-39953ab7190249f7a7fd0e317ec91a09
Source dataset
uspto-grants-1992_01
Patent number
US05082844

Reaction notes

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