5-Iodoisatin → HCID 178485632, compound

HRID 642145

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.[NH:13]([C:15]([C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH3:34])[C:24](=[O:33])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:19][CH:18]=1)=[O:16])[NH2:14]>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:14][NH:13][C:15]([C:17]1[CH:18]=[CH:19][C:20]([N:23]([CH3:34])[C:24](=[O:33])[CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:21][CH:22]=1)=[O:16]

Participants

Conditions

Temperature: 100 °C

Procedure

Following the general method as outlined in Example 1, into a suspension of 5-iodo-1H-indole-2,3dione in acetic acid was added N-[4(hydrazinocarbonyl)phenyl]-N-methyl-3-phenylpropanamide. 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 and water and drying under vacuo at 60° C. overnight gave the title compound (226 mg, 56%) as an orange solid in 96.7% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

temperaturethe reaction mixture was cooled to rt
customa yellow solid precipitated out
filtrationFiltration on a fritté
washwashing with AcOH and water
customdrying under vacuo at 60° C. overnight

Sources & evidence

ORD record: ord-1651d67115414a23b1f1e5644b0678ab
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696231B2

Linked notes

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