Acetic Acid → HCID 86584085, compound

HRID 1168082Notes

Reaction equation

HRID 1168082 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:22])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:21])[CH3:20])[CH:12]=1)[CH:5]=O.[CH2:23]1[S:29][C:27](=[O:28])[NH:26][C:24]1=[O:25].C([O-])(=O)C.[NH2+]1CCCCC1.N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:22])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([CH:19]([CH3:21])[CH3:20])[CH:12]=1)[CH:5]=[C:23]1[S:29][C:27](=[O:28])[NH:26][C:24]1=[O:25]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 3014295Piperidinium acetateHCID 22285675HCID 22285675, compound

Product 1

HCID 86584085HCID 86584085, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of the title compound from Step B (60 mg, 0.18 mmol) and thiazolidinedione (21 mg, 0.18 mmol) in dry toluene (2 ml) was added a catalytic amount of piperidinium acetate which was generated by the addition of piperidine (1.5 mg, 0.018 mmol) and acetic acid (1.1 mg, 0.018 mmol). The mixture was heated to reflux under nitrogen for two hours. The solution was cooled, diluted with ethyl acetate (15 ml), washed with 1 N HCl (3×10 ml) and brine (10 ml), dried, filtered, and concentrated. The residue was purified by preparative TLC (5% methanol in dichloromethane) to give the title compound (26.1 mg) as a yellow solid. MS (APCl−) Calc.: 437.0, Found: 436.1 (M−1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen for two hours
  3. temperatureThe solution was cooled
  4. washwashed with 1 N HCl (3×10 ml) and brine (10 ml)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by preparative TLC (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-acf0631044f04af9b3cff3f5823dbb3d
Source dataset
uspto-grants-2003_09
Patent number
US06620830B2

Reaction notes

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