Thiazolidinedione → 5-[[7-(cyclopropylamino)-5-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methylidene]-1,3-thiazolidine-2,4-dione

HRID 624717Notes

Reaction equation

HRID 624717 reaction equation
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=O)=[C:9]3[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([F:22])[CH:17]=3)[CH:6]=2)[CH2:3][CH2:2]1.N1CCCCC1.[S:29]1[CH2:33][C:32](=[O:34])[NH:31][C:30]1=[O:35]>CCO>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=[C:33]4[S:29][C:30](=[O:35])[NH:31][C:32]4=[O:34])=[C:9]3[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([F:22])[CH:17]=3)[CH:6]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 583144727-(Cyclopropylamino)-5-(2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde

Product 1

HCID 1785184765-[[7-(cyclopropylamino)-5-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methylidene]-1,3-thiazolidine-2,4-dioneYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To 7-(cyclopropylamino)-5-(2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde 30 mg, 0.1 mmol) in EtOH (1 mL) was added piperidine (13 μL, 0.1 mmol), and thiazolidine-2,4-dione (12 mg, 0.1 mmol). The reaction was stirred at 80° C. for 2 hours. The solid formed was isolated by filtration, washed with water then ethanol. The recovered solid was further purified by washing with 20% methanol/dichloromethan to provide 9 mg of 5-((7-(cyclopropylamino)-5-(2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)thiazolidine-2,4-dione (23%). LCMS (M+1=397)

Workup

  1. customThe solid formed
  2. customwas isolated by filtration
  3. washwashed with water
  4. customThe recovered solid was further purified
  5. washby washing with 20% methanol/dichloromethan

Sources & evidence

ORD record
ord-ac78eab9fed64d049e22eb2ad026f297
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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