新产品编号:304253

Chemical Name: N-[1(S)-(4-Aminobenzyl)-2-(4-ethyl-1-piperidinyl)-2-oxoethyl]-4-[1(S)-benzyl-2-(2-hydroxyethoxy)ethylamino]pyridine-3-sulfonamide
CAS No. 200269-57-4
项目整合开发状态: Preclinical
项目研究机构: Novartis (Originator)
合成路线:The condensation of N-(tert-butoxycarbonyl)-4-nitro-L-phenylalanine (I) with 4-ethylpiperiine (II) by means of diisopropylethylamine (DIEA) in dichloromethane gives the corresponding protected piperidide (III),which is treated with TFA to eliminate the carbamate group yielding (IV).The sulfonation of (IV) with 4-chloropyridine-3-sulfonyl chloride (V) by means of DIEA in dichloromethane affords the sulfonamide (VI),which is condensed with 2-(2(S)-amino-3-phenylpropoxy)ethanol (VII) by means of DIEA in ethanol giving the intermediate (VIII).Finally,the reduction of the nitro group of (VIII) with H2 over Pd/C in methanol affords the target compound.

合成路线:The intermediate 2-(2(S)-amino-3-phenylpropoxy)ethanol (VII) has been obtained as follows: The condensation of 2(S)-(dibenzylamino)-3-phenyl-1-propanol (IX) with tert-butyl 2-bromoacetate (X) by means of tetrabutylammonium hydrogen sulfate and NaOH in dichloromethane/water gives 2-[2(S)-(dibenzylamino)-3-phenylpropoxy]acetic acid tert-butyl ester (XI),which is reduced with LiAlH4 in THF yielding 2-[2(S)-(dibenzylamino)-3-phenylpropoxy]ethanol (XII).Finally,this compound is debenzylated by hydrogenation with H2 over Pd/C in methanol/acetic acid affording the target intermediate (VII).