Trifluoroacetic acid → HCID 178497990, compound

HRID 642164Notes

Reaction equation

HRID 642164 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]([C:24]1[CH:50]=[CH:49][C:27]([C:28]([NH:30][CH2:31][C:32]2[CH:48]=[CH:47][C:35]([C:36]([NH:38][NH:39]C(OC(C)(C)C)=O)=[O:37])=[CH:34][CH:33]=2)=[O:29])=[CH:26][CH:25]=1)=[O:23]>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:39][NH:38][C:36]([C:35]1[CH:47]=[CH:48][C:32]([CH2:31][NH:30][C:28]([C:27]2[CH:26]=[CH:25][C:24]([C:22]([O:21][CH3:20])=[O:23])=[CH:50][CH:49]=2)=[O:29])=[CH:33][CH:34]=1)=[O:37]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 886955-IodoisatinHCID 10296107HCID 10296107, compound

Product 1

HCID 178497990HCID 178497990, compoundYield 86%

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-(methoxycarbonyl)benzoyl]amino)methyl)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 614 mg of the title compound (86%) as a yellow solid in 97.9% 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-2b2db22d4f334db09d35e37506588b6f
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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