Thiazolidinedione → HCID 131723183, compound

HRID 841895Notes

Reaction equation

HRID 841895 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH:13]=[C:12]2[CH:26]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:28]1[CH2:32][C:31](=[O:33])[NH:30][C:29]1=[O:34].N1CCCCC1>CCO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH:13]=[C:12]2[CH:26]=[C:32]1[S:28][C:29](=[O:34])[NH:30][C:31]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 22617828HCID 22617828, compound

Product 1

HCID 131723183HCID 131723183, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-benzyloxy-N-(3,4-dichlorophenyl)-indole-3-carbaldehyde (1 eq.), 2,4-thiazolidinedione (1.5 eq.) and piperidine (1.5 eq.) in EtOH was heated to 70° C. for 18 hrs. Volatiles were removed under reduced pressure and the residue was taken up in EtOAc. Addition of ether precipitated the product, which showed the appropriate mass ion and was greater than 60% pure by HPLC (uv readout at 254 nm): isocratic 35:65 H2O/CH3CN. Pure material was obtained by column chromatography on silica gel; (5:3) EtOAc/hexanes. Purity by HPLC was 85%; m\e 510 (M+1); 44% yield.

Workup

  1. customVolatiles were removed under reduced pressure
  2. additionAddition of ether
  3. customprecipitated the product, which
  4. customPure material was obtained by column chromatography on silica gel

Sources & evidence

ORD record
ord-ea145c0c018e437291565ecf369e892b
Source dataset
uspto-grants-2002_04
Patent number
US06372742B1

Reaction notes

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