Potassium Carbonate → 5-[(6-chloropyridin-3-yl)methyl]-2-(2,3-dimethylphenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]pyrido[3,2-e]pyridazin-3-one

HRID 2067106Notes

Reaction equation

HRID 2067106 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=S)[C:11]([C:20]([O:22]CC)=O)=[N:10]2)=[CH:4][CH:3]=1.Cl.[CH3:26][C:27]1[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:28]=1[NH:34][NH2:35].C(=O)([O-])[O-].[K+].[K+]>C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3=[N:35][N:34]([C:28]4[CH:29]=[CH:30][CH:31]=[C:32]([CH3:33])[C:27]=4[CH3:26])[C:20](=[O:22])[C:11]3=[N:10]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27748852,3-Dimethylphenylhydrazine hydrochlorideHCID 86662099Ethyl 1-[(6-chloropyridin-3-yl)methyl]-4-thioxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate

Product 1

HCID 497633445-[(6-chloropyridin-3-yl)methyl]-2-(2,3-dimethylphenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]pyrido[3,2-e]pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Ethyl 1-[(6-chloropyridin-3-yl)methyl]-4-thioxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate (389 mg, 1.08 mmol), (2,3-dimethylphenyl)hydrazine hydrochloride (279 mg, 1.62 mmol, 1.5 equiv) and potassium carbonate (1.49 g, 10.8 mmol, 10 equiv) were combined and placed into an oil bath preheated to 70° C. for 3 hours. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (150 mL, aqueous saturated) and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (1×50 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate containing 5% methanol), providing the titled compound as a deep red solid.

Workup

  1. customplaced into an oil bath
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic extracts were washed with brine (1×50 mL)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate containing 5% methanol)

Sources & evidence

ORD record
ord-673ab726f56b41ad9889bd53d82ff5fd
Source dataset
uspto-grants-2012_10
Patent number
US08293744B2

Reaction notes

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