Triethylamine → HCID 66598885, compound

HRID 1889085Notes

Reaction equation

HRID 1889085 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([N:10]1[CH2:15][CH2:14][NH:13][C:12](=[N:16][NH2:17])[CH2:11]1)=[O:9].C(N(CC)CC)C.[O:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](Cl)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([N:10]1[CH2:15][CH2:14][N:13]2[C:30]([C:26]3[O:25][CH:29]=[CH:28][CH:27]=3)=[N:17][N:16]=[C:12]2[CH2:11]1)=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 178514314HCID 178514314, compound

Product 1

HCID 66598885HCID 66598885, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

4-[(2-chlorophenyl)carbonyl]-2-piperazinone hydrazone (140) (715 mg, 2.83 mmol) and triethylamine (0.986 mL, 7.08 mmol) were dissolved in Dichloromethane (DCM) (10 mL). 2-furancarbonyl chloride (0.306 mL, 3.11 mmol, commercially available from e.g. Sigma-Aldrich, Apollo or Acros) was added and the solution stirred at 25° C. for 4 hr. Solvents were removed in vacuo and the residue was dissolved in n-butanol (10.00 mL). The solution was heated at reflux for 4 hours and the solvents were removed in vacuo. The residue was partitioned between ethyl acetate (50 mL) and saturated sodium bicarbonate solution (25 mL). The aqueous phase was extracted with ethyl acetate (3×25 mL), the combined extracts were washed with water (3×50 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated to a crude solid in 925 mg. The product was purified by flash chromatography (Isolera, 100 g, 0-100% Methanol:Dichloromethane (1:9)/Dichloromethane) to afford product in 260 mg. This was further purified by MDAP to afford product in 85 mg.

Workup

  1. customSolvents were removed in vacuo
  2. dissolutionthe residue was dissolved in n-butanol (10.00 mL)
  3. temperatureThe solution was heated
  4. temperatureat reflux for 4 hours
  5. customthe solvents were removed in vacuo
  6. customThe residue was partitioned between ethyl acetate (50 mL) and saturated sodium bicarbonate solution (25 mL)
  7. extractionThe aqueous phase was extracted with ethyl acetate (3×25 mL)
  8. washthe combined extracts were washed with water (3×50 mL), brine (50 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated to a crude solid in 925 mg
  11. customThe product was purified by flash chromatography (Isolera, 100 g, 0-100% Methanol:Dichloromethane (1:9)/Dichloromethane)
  12. customto afford product in 260 mg
  13. customThis was further purified by MDAP
  14. customto afford product in 85 mg

Sources & evidence

ORD record
ord-991ef78f9416434e888f3a32e20864a2
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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