HCID 2732564, compound → HCID 70045986, compound

HRID 1384463Notes

Reaction equation

HRID 1384463 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[CH2:12]SC2=O)=[CH:5][CH:4]=1.[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH:27]=O)[CH2:21][CH2:20]1>CN(C)C=O>[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[CH:27]=[CH:12][C:13]([NH:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:16])[F:17])=[CH:8][CH:7]=2)=[O:14])[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 2732564HCID 2732564, compoundHCID 27955662-(4-Methylpiperazin-1-yl)benzaldehyde

Product 1

HCID 70045986HCID 70045986, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a flame-dried 3-neck round bottom flask equipped with a magnetic stir bar, sodium hydride (50 mg, 1.25 mmol of a 60% oil dispersion) was washed with hexane and covered with 6.0 mL of anhydrous dimethylformamide (DMF). To this was added a solution of 3-(4-trifluoromethylphenyl)-thiazolidine-2,4-dione (240 mg, 0.92 mmol) and 2-(4-methylpiperazin-1-yl)benzaldehyde (170 mg, 0.84 mmol) in 2 mL of DMF. After stirring at room temperature overnight the mixture was heated to reflux for 4 hours and cooled. The solvent was removed in vacuo and the residue partitioned between saturated aqueous ammonium chloride and chloroform. The organic layer was washed with saturated NaCl, dried and filtered. The residue was absorbed onto silica gel (640 mg) and flash chromatographed on a 4×0.75 in column eluting with ethyl acetate: hexanes (3:1) followed by 100% ethyl acetate. The crude product oil was dissolved in hot EtOAc and allowed to cool to deposit 30 mg of yellow crystals which were filtered and dried, m.p. 207-209° C.

Workup

  1. customIn a flame-dried 3-neck round bottom flask equipped with a magnetic stir bar
  2. washsodium hydride (50 mg, 1.25 mmol of a 60% oil dispersion) was washed with hexane
  3. temperaturewas heated
  4. temperatureto reflux for 4 hours
  5. temperaturecooled
  6. customThe solvent was removed in vacuo
  7. customthe residue partitioned between saturated aqueous ammonium chloride and chloroform
  8. washThe organic layer was washed with saturated NaCl
  9. customdried
  10. filtrationfiltered
  11. customThe residue was absorbed onto silica gel (640 mg) and flash
  12. customchromatographed on a 4×0.75 in column
  13. washeluting with ethyl acetate: hexanes (3:1)
  14. dissolutionThe crude product oil was dissolved in hot EtOAc
  15. temperatureto cool
  16. filtrationwere filtered
  17. customdried

Sources & evidence

ORD record
ord-3450d786b02a4ce3a11d53af2faeff3b
Source dataset
uspto-grants-2001_07
Patent number
US06258953B1

Reaction notes

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