RPR-120844

Chemical Name: 4-[3(S)-(7-Methoxy-N-methylnaphthalen-2-ylsulfonamido)-2-oxopyrrolidin-1-ylmethyl]thiophene-2-carboxamidine
CAS No. 186549-27-9
项目整合开发状态: Preclinical
项目研究机构: Aventis Pharma (Originator)
合成路线:The reduction of 5-bromothiophene-3-carbaldehyde (I) with NaBH4 in THF gives the corresponding carbinol (II),which is treated with Zn(CN)2 and palladium tetrakis(triphenylphosphine) in DMF to yield 4-(hydroxymethyl)thiophene-2-carbonitrile (III).The reaction of (III) with tetrabromomethane and triphenylphosphine affords the corresponding bromomethyl derivative (IV),which is condensed with 3(S)-(tert-butoxycarbonylamino)pyrrolidin-2-one (V) by means of NaH in THF/DMF to give the expected addition product (VI).The deprotection of the amino group of (VI) with HCl in ethyl acetate yields the primary amine (VII),which is acylated with 7-methoxynaphthalene-2-sulfonyl chloride (VIII) and triethylamine in dichloromethane providing the sulfonamide (IX).The methylation of (IX) with methyl iodide and K2CO3 in DMF affords the N-methylsulfonamide (X),which is finally treated first with HCl in ethanol,and then with NH3 in methanol to convert the cyano group of (X) into the amidino group of the target compound.