BMY-14802

BMY-14802, also known as BMS-181100, is a drug with antipsychotic effects which acts as both a sigma receptor antagonist and a 5-HT_1A receptor agonist. It also has affinity for the 5-HT₂ and D₄ receptors. The drug reached phase III clinical trials for the treatment of psychosis but was never marketed.

Synthesis

Patent :
The reaction of 4-chloro-4'-fluorobutyrophenone with ethylene glycol gives the ketal, 2--2--1,3-dioxolane . The reaction of 2-chloro-5-fluoro-4-methylthiopyrimidine with N-carboethoxypiperazine gives ethyl-4--1-piperazine carboxylate, . Catalytic hydrogenation removes the thiomethyl group giving ethyl-4--1-piperazine carboxylate . Acid hydrolysis of the carbamate protecting group gives a secondary amine and hence 5-fluoro-2-pyrimidine . Alkylation of 2 with 7 and subsequent hydrolysis of the ketal protecting group afforded 1--4-butan-1-one . Lastly, reduction of the benzoyl ketone with sodium borohydride gave the alcohol, completing the synthesis of BMY-14802.