SM-256

Chemical Name: 3-[1-[3-(1H-Imidazol-2-ylamino)propyl]-1H-indazol-5-ylcarboxamido]-2(S)-[2,4,6-(trimethyl)phenylsulfonamido]propionic acid
CAS No. 192944-48-2
项目整合开发状态: Preclinical
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:The cyclization of 4-amino-3-methylbenzoic acid ethyl ester (I) by reaction with NaNO2 and HCl catalyzed by NH4BF4 gives indazole-5-carboxylic acid ethyl ester (II),which is condensed with 2-(2-bromoethyl)-1,3-dioxolane (III) by means of sodium hexamethyldisylazane (NaHMDS) yielding the addition product (IV).The hydrolysis of the dioxolane ring of (IV) with AcOH affords the aldehyde (V),which is reductocondensed with 1-tritylimidazole-2-amine (VI) by means of NaBH(OAc)3 providing the intermediate (VII).The hydrolysis of (VII) with NaOH in ethanol/water gives the carboxylic acid (VIII),which is condensed with the 3-aminopropionic ester (IX) by means of DCC and HOBT yielding the amide (X).Finally,the tert-butyl ester of (X) is hydrolyzed with TFA in dichloromethane.