Water → 2,6-dichloro-N-[2-hydroxy-4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-nicotinamide

HRID 1619977Notes

Reaction equation

HRID 1619977 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]([CH3:26])[CH2:21][C:22](=[O:25])[NH:23][N:24]=2)=[CH:15][C:14]=1[OH:27].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]([CH3:26])[CH2:21][C:22](=[O:25])[NH:23][N:24]=2)=[CH:15][C:14]=1[OH:27])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 122639842,6-Dichlorpyridine-3-carbonyl chlorideHCID 179934936-(4-amino-3-hydroxy-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 866890692,6-dichloro-N-[2-hydroxy-4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-nicotinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 8.5 g (0.0405 mol) 2,6-dichloronicotinoyl chloride in 20 ml DMF is slowly added dropwise to a suspension of 8.8 g (0.04 mol) 6-(4-amino-3-hydroxy-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one, 6.9 g (0.05 mol) potassium carbonate and 50 ml DMF and it is then stirred overnight. The reaction mixture is mixed with water, then the aqueous supernatant is decanted off, the residue is washed with water again, filtered off and then purified through silica gel (eluant: ethylene chloride/ethanol).

Workup

  1. customthe aqueous supernatant is decanted off
  2. washthe residue is washed with water again
  3. filtrationfiltered off
  4. custompurified through silica gel (eluant: ethylene chloride/ethanol)

Sources & evidence

ORD record
ord-ad1ec46c20504092aa258f4206056195
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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