SK-549

Chemical Name: 4'-[3-(3-Amidinophenyl)-5-(1-tetrazolylmethyl)-4,5-dihydroisoxazol-5-ylcarboxamido]biphenyl-2-sulfonamide trifluoroacetate
CAS No. 193004-07-8, 193005-13-9 ((-)-enantiomer), 193005-14-0 ((+)-enantiomer)
项目整合开发状态: Biological Testing
项目研究机构: Bristol-Myers Squibb (Originator)
合成路线:The condensation of 2-(bromomethyl)acrylic acid methyl ester (I) with 1H-tetrazole (II) by means of K2CO3 in DMF gives 2-(1-tetrazolylmethyl)acrylic acid methyl ester (III),which is cyclized with 3-cyanobenzaldehyde oxime (IV) by means of NaOCl yielding the oxazoline carboxylic ester (V).The hydrolysis of (V) with LiOH in THF affords the free carboxylic acid (VI),which is condensed with 2-(6-aminopyridin-3-yl)-N-tert-butybenzenesulfonamide (VII) by means of SOCl2 and triethylamine giving the carboxamide (VIII).Finally,this compound is treated with HCl and then with ammonium acetate to eliminate the tert-butyl protecting group and to hydrolyze the cyano group to the target amidino compound.

合成路线:The condensation of 2-(bromomethyl)acrylic acid methyl ester (I) with 1H-tetrazole (II) by means of K2CO3 in DMF gives 2-(1-tetrazolylmethyl)acrylic acid methyl ester (III),which is cyclized with 3-cyanobenzaldehyde oxime (IV) by means of NaOCl yielding the oxazoline carboxylic ester (V).The hydrolysis of (V) with LiOH in THF affords the free carboxylic acid (VI),which is condensed with 4'-amino-N-tert-butylbiphenyl-2-sulfonamide (VII) by means of SOCl2 and triethylamine giving the carboxamide (VIII).Finally,this compound is treated with HCl and then with ammonium acetate to eliminate the tert-butyl protecting group and to hydrolyze the cyano group to the target amidino compound.