Trifluoroacetic acid → HCID 178527269, compound

HRID 352819Notes

Reaction equation

HRID 352819 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:27])[CH:23]=3)[CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH:9]1[CH2:28][CH2:29][C:30]#[N:31])=O)(C)(C)C.[Cl-].[NH4+].[N-:34]=[N+:35]=[N-:36].[Na+].FC(F)(F)C(O)=O>CN(C)C=O.C(Cl)Cl>[Cl:27][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[CH:18]=[C:17]([S:14]([N:11]1[CH2:12][CH2:13][NH:8][CH:9]([CH2:28][CH2:29][C:30]3[NH:36][N:35]=[N:34][N:31]=3)[CH2:10]1)(=[O:15])=[O:16])[CH:26]=[CH:25]2

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22710704HCID 22710704, compound

Product 1

HCID 178527269HCID 178527269, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

In N,N-dimethylformamide (1.5 ml) was dissolved 1-(tert-butoxycarbonyl)-4-[(6-chloronaphthalen-2-yl) sulfonyl]-2-(2-cyanoethyl)piperazine (529 mg), followed by the addition of ammonium chloride (588 mg) and sodium azide (741 mg). The resulting mixture was stirred under heating at 100° C. The reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue and the resulting mixture was washed with water and saturated aqueous NaCl solution, each once. The organic layer thus extracted was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methylene chloride:methanol=50:1), whereby a colorless foam was obtained. The resulting substance was dissolved in methylene chloride (5 ml), followed by the addition of trifluoroacetic acid (5 ml). The mixture was stirred at room temperature for 1 minutes. The reaction mixture was concentrated under reduced pressure. The precipitate thus obtained was washed with diethyl ether and collected by filtration, whereby the title compound (141 mg) was obtained as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washthe resulting mixture was washed with water and saturated aqueous NaCl solution
  4. extractionThe organic layer thus extracted
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by chromatography on a silica gel column (methylene chloride:methanol=50:1), whereby a colorless foam
  9. customwas obtained
  10. stirringThe mixture was stirred at room temperature for 1 minutes
  11. concentrationThe reaction mixture was concentrated under reduced pressure
  12. customThe precipitate thus obtained
  13. washwas washed with diethyl ether
  14. filtrationcollected by filtration, whereby the title compound (141 mg)
  15. customwas obtained as a colorless solid

Sources & evidence

ORD record
ord-0877285b7aa947bcb880c0a340575d85
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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