Thiazolidinedione → HCID 73856760, compound

HRID 2212770Notes

Reaction equation

HRID 2212770 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1[N:7]([CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)=[CH:12][C:11]([Cl:26])=[CH:10][CH:9]=2)=[N+:2]=[N-:3].[S:40]1[CH2:44][C:43](=[O:45])[NH:42][C:41]1=[O:46].N1CCCCC1>CCO>[N:1]([CH2:4][CH2:5][C:6]1[N:7]([CH:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[C:44]3[S:40][C:41](=[O:46])[NH:42][C:43]3=[O:45])=[CH:20][CH:19]=1)=[CH:12][C:11]([Cl:26])=[CH:10][CH:9]=2)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 21962541HCID 21962541, compound

Product 1

HCID 73856760HCID 73856760, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 4-{2-[2-(2-Azido-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethoxy}-benzaldehyde (1.29 g, 2.41 mmole, 1.0 equiv.), 2,4-thiazolidine dione (0.41 g, 3.13 mmole, 1.3 equiv.) and piperidine (0.12 ml, 1.21 mmole, 0.5 equiv.) in EtOH (125 ml) was refluxed overnight. EtOH was removed on vacuo. The residue was diluted in EtOAc and washed with water, then brine. The organic layer was dried over MgSO4 and concentrated, and the residue was chromatographed with 30–35% EtOAc/hexane to obtain 5-(4-{2-[2-(2-Azido-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethoxy}-benzylidene)-thiazolidine-2,4-dione (1.33 g, 87%).

Workup

  1. temperaturewas refluxed overnight
  2. customEtOH was removed on vacuo
  3. additionThe residue was diluted in EtOAc
  4. washwashed with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated
  7. customthe residue was chromatographed with 30–35% EtOAc/hexane

Sources & evidence

ORD record
ord-bb57226b9ac64d0199e0679f934528d6
Source dataset
uspto-grants-2006_09
Patent number
US07101875B2

Reaction notes

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