Thiazolidinedione → HCID 88215764, compound

HRID 2269306Notes

Reaction equation

HRID 2269306 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C@@H:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)[O:16][CH3:17].N1CCCCC1.[S:32]1[CH2:36][C:35](=[O:37])[NH:34][C:33]1=[O:38]>C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C@@H:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[C:36]2[S:32][C:33](=[O:38])[NH:34][C:35]2=[O:37])=[CH:20][CH:19]=1)[O:16][CH3:17]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 131723013HCID 131723013, compound

Product 1

HCID 88215764HCID 88215764, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound of Example 16 (580 mg, 1.7 mmol), piperidine (30 mg, 0.34 mmol) and 2,4thiazolidinedione (405 mg, 3.4 mmol) were combined in ethanol (20 mL) and the resulting solution was refluxed overnight. The solvent was removed in vacuo and the residue was purified on silica gel, eluting with hexane/ethyl acetate (3/1) plus 5% acetic acid, to afford the title compound as a solid (640 mg, 87%). mp 205-206° C. 1HNMR (300 MHz, DMSO-d6): δ2.0 (m, 2H), 2.3 (s, 3H), 2.4 (t, 2H), 3.1 (s, 3H), 4.2 (dd, 1H), 7.4 (m, 5H), 7.6 (d, 2H), 7.7 (s, 1H), 7.9 (m, 2H).

Workup

  1. temperaturethe resulting solution was refluxed overnight
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified on silica gel
  4. washeluting with hexane/ethyl acetate (3/1) plus 5% acetic acid

Sources & evidence

ORD record
ord-062d933aebc141b686292e4e2ff5b687
Source dataset
uspto-grants-2001_12
Patent number
US06329408B1

Reaction notes

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