SC-276

Chemical Name: 4-[4-(Phenylsulfanyl)phenylsulfonyl]-1-(2-propynyl)piperidine-4-carbohydroxamic acid hydrochloride
CAS No. 226388-60-9, 226393-68-6 (free base), 226393-69-7 (monomethane sulfonate salt)
项目整合开发状态: Preclinical
项目研究机构: Pfizer (Originator)
合成路线:Ethyl isonipecotate (I) was protected as the N-Boc derivative (II) employing di-tert-butyl dicarbonate.Sulfenylation of the lithium enolate of ester (II) with the disulfide (IV),generated from the oxidation of 4-fluorothiophenol (III),furnished the phenylsulfanyl derivative (V).Thioether (V) was then oxidized to the corresponding sulfone (VI) by means of meta-chloroperbenzoic acid.After acidic Boc group cleavage in (VI),the resultant piperidine (VII) was alkylated with propargyl bromide (VIII) to produce the N-propargyl piperidine (IX).

合成路线:Displacement of the 4-fluoro group of (IX) with thiophenol (X) in the presence of K2CO3 led to the diaryl sulfide (XI).Acid (XII),prepared by alkaline hydrolysis of ester (XI),was then coupled to O-tetrahydropyranyl hydroxylamine (XIII) by means of EDC to furnish (XIV).Finally,acidic cleavage of the tetrahydropyranyl moiety produced the corresponding hydroxamic acid.