Water → 3-(1-methyl-1H-pyrazol-5-yl)-1-phenyl-5-(quinolin-2-ylmethoxy)pyridazin-4(1H)-one

HRID 333744Notes

Reaction equation

HRID 333744 reaction equation
[OH:1][C:2]1[C:3](=[O:20])[C:4]([C:14]2[N:18]([CH3:19])[N:17]=[CH:16][CH:15]=2)=[N:5][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl.Cl[CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=1.O>CN(C)C=O>[CH3:19][N:18]1[C:14]([C:4]2[C:3](=[O:20])[C:2]([O:1][CH2:29][C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)=[CH:7][N:6]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:5]=2)=[CH:15][CH:16]=[N:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 895867585-hydroxy-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-one

Product 1

HCID 895864983-(1-methyl-1H-pyrazol-5-yl)-1-phenyl-5-(quinolin-2-ylmethoxy)pyridazin-4(1H)-oneYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-hydroxy-3-(1-methyl-1H-pyrazol-5-yl)-1-phenylpyridazin-4(1H)-one (268 mg) in dimethylformamide (10 mL) was added cesium carbonate (782 mg), 2-(chloromethyl)quinoline hydrochloride (236 mg) was added with stirring under ice-cooling, and the mixture was allowed to warm to room temperature and stirred for 64 hr. Water was added to the reaction mixture and the mixture was stirred for 1 hr. The precipitated crystals were collected by filtration, washed successively with water, methanol and diisopropyl ether, and dried to give the title compound (226 mg) as a white solid.

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringstirred for 64 hr
  4. stirringthe mixture was stirred for 1 hr
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed successively with water, methanol and diisopropyl ether
  7. customdried

Sources & evidence

ORD record
ord-0955f19750444628a734b417dc7f4f7a
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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