Water → N-Methyl-3-(6-oxo-1,6-dihydro-pyridazin-4-yl)-benzamide

HRID 1097317Notes

Reaction equation

HRID 1097317 reaction equation
Cl[C:2]1[CH:7]=[N:6][NH:5][C:4](=[O:8])[CH:3]=1.[CH3:9][NH:10][C:11]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)=[O:12].O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CCOC(C)=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO>[CH3:9][NH:10][C:11](=[O:12])[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([C:2]2[CH:7]=[N:6][NH:5][C:4](=[O:8])[CH:3]=2)[CH:18]=1

Participants

9

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27735243-(Methylcarbamoyl)benzeneboronic acidHCID 199057185-Chloropyridazin-3(2H)-one

Product 1

HCID 59443494N-Methyl-3-(6-oxo-1,6-dihydro-pyridazin-4-yl)-benzamide

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolventHCID 22728543Water ethylacetateSolvent

Procedure

5-Chloro-pyridazin-3-one (1 eq, 5.06 mmol, 660 mg) and 3-(N-Methylaminocarbonyl)phenyl boronic acid (1.1 eq, 5.56 mmol, 996 mg) are dissolved in dioxane (4 ml), water (2 ml) and EtOH (2 ml) and K2CO3 (2 eq, 10.1 mmol, 1.40 g) is added. Pd(PPh3)4 (0.1 eq, 0.5 mmol, 584 mg) is then added and the reaction mixture is heated using microwave radiation at 140° C. for 20 min. The reaction mixture is diluted with EtOAc/H2O and filtered. The organic layer is then separated and the aqueous layer is extracted with EtOAc (2×20 ml). The organic layer is washed with NaHCO3, brine, dried over MgSO4, filtered and evaporated to dryness to yield N-Methyl-3-(6-oxo-1,6-dihydro-pyridazin-4-yl)-benzamide as a white solid which did not require further purification; [M+H]+=230

Workup

  1. temperaturethe reaction mixture is heated
  2. customat 140° C.
  3. customfor 20 min
  4. filtrationfiltered
  5. customThe organic layer is then separated
  6. extractionthe aqueous layer is extracted with EtOAc (2×20 ml)
  7. washThe organic layer is washed with NaHCO3, brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-b7135b2aaafb408a8f5091124285cfc5
Source dataset
uspto-grants-2012_03
Patent number
US08143253B2

Reaction notes

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