Thiazolidinedione → HCID 58312813, compound

HRID 1751181Notes

Reaction equation

HRID 1751181 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[C:4]([O:10][CH2:11][CH2:12][O:13][CH3:14])[N:3]=1.[S:15]1[CH2:19][C:18](=[O:20])[NH:17][C:16]1=[O:21].[C:22]1([CH3:34])[CH:27]=[CH:26][C:25]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[CH:24][CH:23]=1>C(O)C>[CH3:14][O:13][CH2:12][CH2:11][O:10][C:4]1[N:3]=[C:2]([N:31]2[CH2:32][CH2:33][N:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:34])=[CH:23][CH:24]=3)[CH2:29][CH2:30]2)[N:7]=[C:6](/[CH:8]=[C:19]2/[C:18](=[O:20])[NH:17][C:16](=[O:21])[S:15]/2)[CH:5]=1

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 831131-(p-Tolyl)piperazineHCID 58312971HCID 58312971, compound

Product 1

HCID 58312813HCID 58312813, compoundYield 104.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Crude 2-chloro-6-(2-methoxyethoxy)pyrimidine-4-carbaldehyde (sad105-052, 41.9 mg) was dissolved in ethanol (1.5 mL) and was added to a 10 mL vial containing the thiazolidine-dione (21.3 mg, 0.18 mmol) and the 1-(p-tolyl)piperazine (39.3 mg, 0.18 mmol). The reaction mixture was shaken at 80° C. for 15.5 h. LC-MS showed a peak with the desired mass at 2.18 min (M+1=456). The solvent was concentrated under reduced pressure and the residue was dissolved in EtOAc (20 mL) and washed with saturated NaHCO3 (10 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to provide 85.7 mg of brown oil. Purification by flash chromatography (SiO2,10 g, Hexanes/EtOAc 9:1 to 6:4 to 1:1) provided 11.5 mg (13.9% 2 steps, 83 mg theoretical) of pure (Z)-5-((6-(2-methoxyethoxy)-2-(4-(p-tolyl)piperazin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione as a yellow solid.

Workup

  1. additionwas added to a 10 mL
  2. customat 2.18 min
  3. concentrationThe solvent was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in EtOAc (20 mL)
  5. washwashed with saturated NaHCO3 (10 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4cfbfcd1162a4d5faa23986ae9af53cd
Source dataset
uspto-grants-2015_10
Patent number
US09157077B2

Reaction notes

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