HCID 20435986, compound → HCID 20435990, compound

HRID 1154045Notes

Reaction equation

HRID 1154045 reaction equation
[CH2:1]([C:8]1([CH2:23][CH2:24]I)[C:20](=[O:21])[N:11]2[CH2:12][CH:13]=[CH:14][CH:15]([C:16]([O:18][CH3:19])=[O:17])[N:10]2[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]([O-:29])(=[S:28])[CH3:27].[K+]>CC(C)=O>[C:26]([S:28][CH2:24][CH2:23][C:8]1([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:20](=[O:21])[N:11]2[CH2:12][CH:13]=[CH:14][CH:15]([C:16]([O:18][CH3:19])=[O:17])[N:10]2[C:9]1=[O:22])(=[O:29])[CH3:27]

Participants

4

Reactant 2

HCID 20435986HCID 20435986, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 20435990HCID 20435990, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(a) A mixture of 5.2 g of methyl 2-benzyl-2,3,5,8-tetrahydro-2-(2-iodoethyl)-1,3-dioxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate and 1.31 g of potassium thioacetate in 150 ml of acetone was stirred at room temperature for 8 hours. The solvent was removed by evaporation and the residue was partitioned between dichloromethane and water. The organic phase was separated, dried over magnesium sulfate and evaporated to give methyl 2-(2-acetylthioethyl)-2-benzyl-2,3,5,8-tetrahydro-1,3-dioxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate as a mixture of diastereomers. Trituration with diethyl ether gave 3.5 g of diasteremoer B in the form of a white solid having a melting point of 161°-162° C. (from ethylacetate).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was partitioned between dichloromethane and water
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-0b20c38e289e46f7a6378ee231494b58
Source dataset
uspto-grants-1984_12
Patent number
US04487929

Reaction notes

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