HCID 20435995, compound → tert.butyl 2-acetylthiomethyl-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate

HRID 1154051Notes

Reaction equation

HRID 1154051 reaction equation
Br[CH2:2][CH:3]1[CH2:18][N:6]2[CH2:7][CH2:8][CH2:9][CH:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:5]2[C:4]1=[O:19].[C:20]([O-:23])(=[S:22])[CH3:21].[K+]>CC(C)=O>[C:20]([S:22][CH2:2][CH:3]1[CH2:18][N:6]2[CH2:7][CH2:8][CH2:9][CH:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:5]2[C:4]1=[O:19])(=[O:23])[CH3:21]

Participants

4

Reactant 2

HCID 20435995HCID 20435995, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 20435955tert.butyl 2-acetylthiomethyl-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylateYield 76.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.42 g of tert.butyl 2-bromomethyl-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate (diastereomer A) and 0.58 g of potassium thioacetate were stirred at room temperature in 20 ml of acetone for 17 hours. The solvent was removed by evaporation, the residue was diluted with 100 ml of ethyl acetate, the mixture was washed three times with sodium chloride solution, dried over magnesium sulfate and evaporated. After recrystallization of the residue from ethyl acetate/hexane, there were obtained 1.07 g of tert.-butyl 2-acetylthiomethyl-hexahydro-3-oxo-1H-pyrazolo[1,2-a]-pyridazine-5-carboxylate (diastereomer A) having a melting point of 92°-93° C. (from ethyl acetate/hexane).

Workup

  1. customThe solvent was removed by evaporation
  2. additionthe residue was diluted with 100 ml of ethyl acetate
  3. washthe mixture was washed three times with sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customAfter recrystallization of the residue from ethyl acetate/hexane

Sources & evidence

ORD record
ord-188d5f0baebd487aa02eeee85da987af
Source dataset
uspto-grants-1984_12
Patent number
US04487929

Reaction notes

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