3-Chloro-6-hydrazinopyridazine → HCID 23143477, compound

HRID 1437267Notes

Reaction equation

HRID 1437267 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4](=O)[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=1)=O.[Cl:19][C:20]1[N:21]=[N:22][C:23]([NH:26][NH2:27])=[CH:24][CH:25]=1>CO>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([N:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[N:26]([C:23]2[N:22]=[N:21][C:20]([Cl:19])=[CH:25][CH:24]=2)[N:27]=1)=[O:18]

Participants

4

Reactant 2

HCID 1007873-Chloro-6-hydrazinopyridazineHCID 12691357HCID 12691357, compound

Product 1

HCID 23143477HCID 23143477, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above-obtained 4-(4-dimethylaminophenyl)-2,4-dioxobutanoic acid methyl ester (742 mg) and 3-chloro-6-hydrazinopyridazine (473 mg) in methanol (30 mL) was refluxed under heat for 18 hours, and then cooled in air. The reaction solvent was removed under reduced pressure, and the residue was partitioned by use of saturated aqueous sodium hydrogencarbonate and chloroform. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, and the residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give 1-(6-chloro-3-pyridazinyl)-5-(4-dimethylaminophenyl)pyrazole-3-carboxylic acid methyl ester as a solid (679 mg, 63%).

Workup

  1. temperatureunder heat for 18 hours
  2. temperaturecooled in air
  3. customThe reaction solvent was removed under reduced pressure
  4. customthe residue was partitioned by use of saturated aqueous sodium hydrogencarbonate and chloroform
  5. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  6. filtrationfollowed by filtration
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-6793590571054d4abc47b2b6068df472
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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