Thiazolidinedione → HCID 75288718, compound

HRID 383658Notes

Reaction equation

HRID 383658 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][N:6]2[CH:11]=[CH:10][C:9]([C:12]3[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=3)[C:15]([O-:17])=[O:16])=[N:8][C:7]=12)=O.[S:21]1[CH2:25][C:24](=[O:26])[NH:23][C:22]1=[O:27].N1CCCC[CH2:29]1>CCO>[O:27]=[C:22]1[NH:23][C:24](=[O:26])[C:25](=[CH:1][C:3]2[CH:4]=[N:5][N:6]3[CH:11]=[CH:10][C:9]([C:12]4[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=4)[C:15]([O:17][CH3:29])=[O:16])=[N:8][C:7]=23)[S:21]1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 86649381HCID 86649381, compound

Product 1

HCID 75288718HCID 75288718, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To 3-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)benzoate (27 mg, 0.096 mmol) in 0.5 mL EtOH was added 2,4-thiazolidinedione (11 mg, 0.096 mmol) and piperidine (9.5 μL, 0.096 mmol). The mixture was stirred at 50° C. overnight. The solid formed was isolated by filtration and air dried to yield 27 mg methyl 3-(3-((2,4-dioxothiazolidin-5-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-yl)benzoate as an orange solid (74% yield). LCMS (M+1=381)

Workup

  1. customThe solid formed
  2. customwas isolated by filtration and air
  3. customdried

Sources & evidence

ORD record
ord-31458365e9f34ab9a76db668a16cf0da
Source dataset
uspto-grants-2013_02
Patent number
US08367681B2

Reaction notes

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