Trifluoroacetic acid → HCID 19372789, compound

HRID 129224Notes

Reaction equation

HRID 129224 reaction equation
Cl.[NH2:2][CH:3]1[CH2:26][C:7]2=[CH:8][N:9]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C:10]3[CH:11]=[CH:12][C:13]([O:14][CH3:15])=[C:5]([C:6]=32)[C:4]1=[O:27].[F:28][C:29]([F:34])([F:33])[C:30](O)=[O:31].C(N(CC)CC)C>ClCCl>[CH3:15][O:14][C:13]1[CH:12]=[CH:11][C:10]2[N:9]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:8]=[C:7]3[CH2:26][CH:3]([NH:2][C:30](=[O:31])[C:29]([F:34])([F:33])[F:28])[C:4](=[O:27])[C:5]=1[C:6]=23

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 19372801HCID 19372801, compound

Product 1

HCID 19372789HCID 19372789, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-amino-3,4-dihydro-6-methoxy-1-p-toluenesulfonylbenz[cd]indol-5(1H)-one hydrochloride (1.45 g, 3.50 mmol) in dichloromethane (30 ml) were added, while stirring under ice-cooling, anhydrous trifluoroacetic acid (0.61 ml, 4.27 mmol) and triethylamine (1.18 ml, 16.1 mmol). The mixture was stirred for 30 minutes as it was. After completion of the reaction, the reaction mixture was subjected to distillation under reduced pressure. The residue was shaken together with ethyl acetate (40 ml)-1N HCl (30 ml) to allow two layers to be formed. The organic layer was washed with an aqueous saline solution and dried (anhydrous Na2SO4). The solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate-n-hexane to afford the title compound (1.2 g, 73%, m.p.189°-190° C.)

Workup

  1. additionwere added
  2. temperaturecooling
  3. stirringThe mixture was stirred for 30 minutes as it
  4. customAfter completion of the reaction
  5. distillationthe reaction mixture was subjected to distillation under reduced pressure
  6. stirringThe residue was shaken together with ethyl acetate (40 ml)-1N HCl (30 ml)
  7. customto be formed
  8. washThe organic layer was washed with an aqueous saline solution
  9. dry with materialdried (anhydrous Na2SO4)
  10. distillationThe solvent was distilled off under reduced pressure
  11. customThe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-5db5b489605349bcb6b59c753c4a0d29
Source dataset
uspto-grants-1995_11
Patent number
US05466689

Reaction notes

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