Trifluoroacetic acid → HCID 178500553, compound

HRID 642150Notes

Reaction equation

HRID 642150 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.C(O)(C(F)(F)F)=O.[CH3:20][O:21][C:22](=[O:45])[CH2:23][CH2:24][C:25]([NH:27][C:28]1[CH:44]=[CH:43][C:31]([C:32]([NH:34][NH:35]C(OC(C)(C)C)=O)=[O:33])=[CH:30][CH:29]=1)=[O:26]>C(O)(=O)C>[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[N:35][NH:34][C:32]([C:31]1[CH:30]=[CH:29][C:28]([NH:27][C:25](=[O:26])[CH2:24][CH2:23][C:22]([O:21][CH3:20])=[O:45])=[CH:44][CH:43]=1)=[O:33]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 886955-IodoisatinHCID 9925313Tert-butyl 2-{4-[(4-methoxy-4-oxobutanoyl)amino]benzoyl}hydrazinecarboxylate

Product 1

HCID 178500553HCID 178500553, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Following the general method as outlined in Example 1, into a suspension of 5-iodo-1H-indole-2,3-dione in acetic acid in the presence of 5% TFA was added tert-butyl 2-{4-[(4-methoxy-4-oxobutanoyl)amino]benzoyl}hydrazinecarboxylate. After stirring at 100° C., the reaction mixture was cooled to rt and an orange solid precipitated out. Filtration on a fritté, washing with AcOH, water and drying under vacuo at 60° C. for 60 min gave 89 mg of the title compound (92%) as an orange solid in 98.8% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. temperaturethe reaction mixture was cooled to rt
  2. customan orange solid precipitated out
  3. filtrationFiltration on a fritté
  4. washwashing with AcOH, water
  5. customdrying under vacuo at 60° C. for 60 min

Sources & evidence

ORD record
ord-a546d47e53734b7ba45810e8957279c8
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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