Synthesis of the Key Intermediate of SM-406 (Xevinapant) and Its Analogues

Efficient methods for the synthesis of three dipeptide mimetics with diazabicycloalkanone amino acid scaffolds were developed. Among them, compound 3, which contains a 1,5diazabicyclo[6,3,0]dodecanone amino acid core structure, was used as the key intermediate of a clinical staged IAP inhibitor SM-406 (Xevinapant). Compared with the reported methods for the synthesis of compound 3 and its derivatives, our method is more efficient and more suitable for large scale preparation.

Automated summary

Efficient methods for synthesizing three dipeptide mimetics with diazabicycloalkanone amino acid scaffolds were developed, with compound 3 serving as a key intermediate for a clinical staged IAP inhibitor. Compared to reported methods, the new method is more efficient and suitable for large scale preparation.