Zhao Tian-tia
2014
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Journal
Pharmaceutical Journal of Chinese People's Liberation Army
Abstract
Objective To improve the synthesis of a novel S1P1 agonist CYM-5442. Methods4-carbonitrile-1-indanone( 1) was prepared from 3-( 2-cyanophenyl) propanoic acid which was the starting material via FriedelCrafts acylation reaction of 3-( 2-cyanophenyl) propanoic acid with anhydrous AlCl3 and NaCl of neat reagents in direct heating under the condition of solid phase. Intermediate 3 was obtained by reaction of NH2OH·HCl with intermediate 2 obtained by reduction reaction with NaBH4. Intermediate 4 was prepared by reaction of intermediate 3 with 3,4-diethoxybenzoic acid,EDCI and HOBt. Finally,CYM-5442 was obtained by reaction of compound( 4)with SOCl2 and aminoethanol. Results The overall yield of the five steps for the target product was 11. 3%. Moreover,the structure of the product was characterized by means of1H-NMR spectroscopy and ESI-MS. Conclusion This synthesis method of CYM-5442 is economical in that 3-( 2-cyanophenyl) propanoic acid is used as the starting material which is cheap and easily available. Moreover,the method is simple and the overall yield is good.