1,2-Dichloroethane → (5s)-2-(2-(4-Tert-butylpiperazin-1-yl)-3,5-difluorophenyl)-3-(3,3-dimethylbutyl)-5-(2-oxo-2-(4-(2-oxo-2,3-dihydro-1h-benzo[d]imidazol-1-yl)piperidin-1-yl)ethyl)thiazolidin-4-one

Participants

Reaction Steps

2-((5S)-2-(2-(4-tert-Butylpiperazin-1-yl)-3,5-difluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid (100 mg, 0.2 mmol), EDC (40 mg, 0.2 mmol), DIEA (52 mg, 0.4 mmol) and 1-(piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one bis HCl salt (60 mg, 0.2 mmol) were combined in DMF and let stir for 3 days. The mixture was then poured into EtOAc/sat'd NaHCO3. The organic layer was dried and concentrated to a solid and purified by reverse phase HPLC. Pure fractions were poured into EtOAc/1N NaOH and the organic layer was dried and concentrated to a solid, which was taken up in methanol. Then 4N HCl in dioxane was added. This solution was concentrated to give (5S)-2-(2-(4-tert-butylpiperazin-1-yl)-3,5-difluorophenyl)-3-(3,3-dimethylbutyl)-5-(2-oxo-2-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-1-yl)ethyl)thiazolidin-4-one as a white solid (24 mg., 0.03 mmol, 15% yield). LC/MS MH+ 697.97.

Provenance & Evidence