Thiazolidinedione → HCID 86605784, compound

HRID 2221946Notes

Reaction equation

HRID 2221946 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:36])=[C:9]([CH2:11][O:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][O:18][C:19]3[C:23]([CH:24]=O)=[CH:22][N:21]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:20]=3)=[CH:15][C:14]=2[O:34][CH3:35])[N:10]=1.[S:37]1[CH2:41][C:40](=[O:42])[NH:39][C:38]1=[O:43].N1CCCCC1>C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:36])=[C:9]([CH2:11][O:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][O:18][C:19]3[C:23](/[CH:24]=[C:41]4/[C:40](=[O:42])[NH:39][C:38](=[O:43])[S:37]/4)=[CH:22][N:21]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:20]=3)=[CH:15][C:14]=2[O:34][CH3:35])[N:10]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 866057753-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 86605784HCID 86605784, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazole-4-carbaldehyde (1.10 g), 1,3-thiazolidine-2,4-dione (0.27 g), piperidine (0.04 g) and ethanol (30 mL) was heated under reflux for 3 hrs. The reaction mixture was concentrated, and the obtained crystals were washed with ethanol to give (5Z)-5-({3-[(4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}methylene)-1,3-thiazolidine-2,4-dione as yellow crystals (1.13 g, yield 84%). Recrystallization from tetrahydrofuran-hexane gave yellow prism crystals. melting point: 252-253° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hrs
  3. concentrationThe reaction mixture was concentrated
  4. washthe obtained crystals were washed with ethanol

Sources & evidence

ORD record
ord-7341eb60104847bb953343e12eea033b
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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