3,3-Dimethylbutylamine → 2-((5S)-2-(2-(4-tert-butylpiperazin-1-yl)-3,5-difluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

3,3-Dimethylbutan-1-amine (0.7 g, 6.8 mmol) and 2-(4-tert-butylpiperazin-1-yl)-3,5-difluorobenzaldehyde (0.96 g, 3.4 mmol) were combined in toluene and heated to reflux overnight with a Dean-Stark trap attached. The reaction mixture was concentrated to a brown oil. This oil was redissolved in toluene and (S)-2-mercaptosuccinic acid (510 mg, 3.4 mmol) was added. The reaction mixture was heated at 80° C. for 16 hrs., concentrated to an oil, and triturated with ether to give a beige solid, which was filtered off and dried to give 2-((5S)-2-(2-(4-tert-butylpiperazin-1-yl)-3,5-difluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid (0.45 g, 0.92 mmol, 27% yield) as a solid. LC/MS MH+ 498.45.

Provenance & Evidence