2-[(2,5-Dichlorophenoxy)methyl]oxirane → 6-[4-[2-[3-(2,5-dichlorophenoxy)-2-hydroxypropylamino]-2-methylpropylamino]phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

HRID 1905422Notes

Reaction equation

HRID 1905422 reaction equation
[NH2:1][C:2]([CH3:20])([CH3:19])[CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]([CH3:18])[CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:7][CH:6]=1.[Cl:21][C:22]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:23]=1[O:24][CH2:25][CH:26]1[O:28][CH2:27]1>C(O)(C)(C)C>[Cl:21][C:22]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:23]=1[O:24][CH2:25][CH:26]([OH:28])[CH2:27][NH:1][C:2]([CH3:19])([CH3:20])[CH2:3][NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]([CH3:18])[CH2:13][C:14](=[O:17])[NH:15][N:16]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 37931642-[(2,5-Dichlorophenoxy)methyl]oxiraneHCID 106123876-[4-(2-amino-2-methylpropyl amino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 105771106-[4-[2-[3-(2,5-dichlorophenoxy)-2-hydroxypropylamino]-2-methylpropylamino]phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinoneYield 88.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 6-[4-(2-amino-2-methylpropylamino)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (3 g), 1-(2,5-dichlorophenoxy)-2,3-epoxypropane (2.4 g) and t-butanol (100 ml) was stirred at 65° to 70° C. for 24 hours. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Wakogel C-200, 120 g). From the chloroform/methanol (=50/1) eluted portion, 6-[4-[2-[3-(2,5-dichlorophenoxy)-2-hydroxypropylamino]-2-methylpropylamino]phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (4.77 g) was obtained.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (Wakogel C-200, 120 g)
  3. washFrom the chloroform/methanol (=50/1) eluted portion

Sources & evidence

ORD record
ord-a4ad83bda8454de497d1ddb44b8e9c1a
Source dataset
uspto-grants-1989_06
Patent number
US04843072

Reaction notes

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