Trifluoroacetic acid → HCID 178500352, compound

HRID 642154Notes

Reaction equation

HRID 642154 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:47])[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([NH:29][C:30]1[CH:46]=[CH:45][C:33]([C:34]([NH:36][NH:37]C(OC(C)(C)C)=O)=[O:35])=[CH:32][CH:31]=1)=[O:28]>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:37][NH:36][C:34]([C:33]1[CH:32]=[CH:31][C:30]([NH:29][C:27](=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][C:22]([O:21][CH3:20])=[O:47])=[CH:46][CH:45]=1)=[O:35]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 886955-IodoisatinHCID 10293973Tert-butyl 2-{4-[(6-methoxy-6-oxohexanoyl)amino]benzoyl)hydrazinecarboxylate

Product 1

HCID 178500352HCID 178500352, compoundYield 82%

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-[(6-methoxy-6-oxohexanoyl)amino]benzoyl)hydrazinecarboxylate. After stirring at 100° C., the reaction mixture was cooled to rt and a yellow solid precipitated out. Filtration on a fritté, washing with AcOH, water and drying under vacuo at 70° C. for 15 hrs gave 496 mg of the title compound (82%) as a yellow solid in 99.5% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. temperaturethe reaction mixture was cooled to rt
  2. customa yellow solid precipitated out
  3. filtrationFiltration on a fritté
  4. washwashing with AcOH, water
  5. customdrying under vacuo at 70° C. for 15 hrs

Sources & evidence

ORD record
ord-b0465669319e44f8b98b22a7ae0b4bbc
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

Loading…