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 1588228Notes

Reaction equation

HRID 1588228 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]pheyl]-4,5-dihydro-3(2H)-pyridazinone.

Workup

  1. temperaturethe solution was heated

Sources & evidence

ORD record
ord-6343ee1b2ed342f6945f7fb083a63dd6
Source dataset
uspto-grants-1993_06
Patent number
US05221674

Reaction notes

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