4-Iodobenzoic acid → 1h-Pyrrole-2-carboxylic acid, 1-methyl-2-(4-iodobenzoyl)hydrazide

HRID 31426

Reaction equation

[CH3:1][N:2]([C:4]([C:6]1[NH:7][CH:8]=[CH:9][CH:10]=1)=[O:5])[NH2:3].C1C=CC2N(O)N=NC=2C=1.[I:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)CCl>[CH3:1][N:2]([C:4]([C:6]1[NH:7][CH:8]=[CH:9][CH:10]=1)=[O:5])[NH:3][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:22]([I:21])=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 40 °C

Procedure

1H-Pyrrole-2-carboxylic acid, 1-methyl-hydrazide (139 mg), EDC (230 mg), HOBt (162 mg), 4-iodobenzoic acid (248 mg) and DIPEA (0.21 ml) were mixed in DMF (3 ml). The reaction was heated at 40° C. for 6 hours, the DMF was evaporated under vacuum and the residue applied to a bond-elut (silica) and eluted with an ethyl acetate/cyclohexane gradient to give, after evaporation of the solvent, 1H-pyrrole-2-carboxylic acid, 1-methyl-2-(4-iodobenzoyl)hydrazide.

Workup

customthe DMF was evaporated under vacuum
washeluted with an ethyl acetate/cyclohexane gradient
customto give
customafter evaporation of the solvent, 1H-pyrrole-2-carboxylic acid, 1-methyl-2-(4-iodobenzoyl)hydrazide

Sources & evidence

ORD record: ord-47dc77586e68474399b3b016fddb9e26
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425555B2

Linked notes

Loading…