ABSTRACT: TG4-155 has biological applications by antagonizing the prostaglandin EP2 receptor in the brain and prostate.[i] This potential API may serve as a treatment for both epilepsy and cancer.2 In this research, 2-methyl-1H-indole (1) and 2-chloroethylamine hydrochloride (2), were condensed in the presence sodium hydroxide and tetrabutylammonium hydrogen sulfate (TBAHS) under toluene reflux to form 2-(2-methyl-indole-1-yl)ethanamine (3). After flash chromatography, (3) was activated with CDI and combined with 3,4,5-trimethoxycinnamic acid (4) to yield (2E)-N-[2-(2-methyl-1H-indol-1-yl)ethyl]-3-(3,4,5-trimethoxyphenyl)-2-propenamide, TG4-155 (5). Following flash chromatography (FC) and recrystallization, the maximum yield for (5) was 60% (98% pure by HPLC). FTIR, 1HNMR, GCMS, HPLC, MP, and TLC were used to evaluate raw materials and products.

TG4-155 from 2-methylindole, 2-chloroethylamine, and 3,4,5-trimethoxycinnamic acid via alkylation followed by CDI facilitated amidation

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