Acetic Acid → HCID 178500268, compound

HRID 642156Notes

Reaction equation

HRID 642156 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:13]([OH:19])([C:15](F)(F)F)=[O:14].COC(=O)CC[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([NH:32][C:33]1[CH:49]=[CH:48][C:36]([C:37]([NH:39][NH:40]C(OC(C)(C)C)=O)=[O:38])=[CH:35][CH:34]=1)=[O:31].[C:51](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:40][NH:39][C:37]([C:36]1[CH:48]=[CH:49][C:33]([NH:32][C:30](=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:15][C:13]([O:19][CH3:51])=[O:14])=[CH:34][CH:35]=1)=[O:38]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 886955-IodoisatinHCID 10203325HCID 10203325, compound

Product 1

HCID 178500268HCID 178500268, compoundYield 95%

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-[(9-methoxy-9-oxononanoyl)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 21 hrs gave 611 mg of the title compound (95%) as a yellow solid in 98.1% 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 21 hrs

Sources & evidence

ORD record
ord-7b7155ec18b84a0ca97158a6a2d5fdc8
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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