合成路线1

Cenicriviroc mesilate can be prepared by two related strategies:
In one strategy, chlorination of benzazocine-5-carboxylic acid derivative (I) with (COCl)2 (1, 2) or SOCl2 in THF (3) yields the corresponding acyl chloride (II) (1-3), which then couples with S-Cbz-4-thioaniline (III) in the presence of Et3N in THF to afford, after hydrolysis of the Cbz group with NaOH in MeOH, the corresponding N-(4-sulfanylphenyl)amide (IV). Subsequent S-alkylation of thiol (IV) with 5-(chloromethyl)-1-propylimidazole (V) in the presence of NaOH in MeOH yields thioether (VI). After oxidation of (VI) with mCPBA in CH2Cl2, the resulting racemic sulfoxide is resolved employing chiral HPLC to furnish the target (S)-enantiomer, which is then treated with MsOH in EtOAc to afford cenicriviroc mesilate (2). In another strategy, acyl chloride (II) couples with the substituted aniline (VII) in the presence of DIEA in THF (1) or Et3N in THF (3) to yield cenicriviroc, which is then reacted with MsOH in methyl isobutyl ketone, producing the target cenicriviroc mesilate (1, 3). Scheme 1.