ST-368

Chemical Name: (-)-3-(3-Amino-4-chlorophenyl)-5-(methylsulfonamidomethyl)-N-[5-(2-sulfamoylphenyl)pyridin-2-yl]-4,5-dihydroisoxazole-5-carboxamide
项目整合开发状态: Preclinical
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:Conversion of the bromo derivative (I) into the corresponding azido compound (II) is performed by treatment with NaN3 in DMSO.Separately,aldehyde (III) is treated with hydroxylamine to provide oxime (IV),which is then condensed with derivative (II) by means of bleach in CH2Cl2 to furnish isoxazoline derivative (V).Hydrolysis of the methyl ester of (V) by means of LiOH in THF affords carboxylic acid (VI),which is treated with SOCl2 and then condensed with amine (VII) by means of Et3N to give carboxamide (VIII).Reduction of the azido moiety of (VIII) by means of P(OEt)3 in THF yields amine (IX),which is then derivatized by reaction with mesyl chloride (MeSO2Cl) to provide mesylate (X).Finally,the desired compound is obtained by treatment of (X) with TFA for tert-butyl group removal,followed by reduction of the nitro moiety with SnCl2.