MEN-11149

Chemical Name: (1R,2S)-2-(1H-Indol-3-ylcarboxamido)-N-[1-[N-methyl-2-(4-methylphenyl)acetamido]-2-(2-naphthyl)ethyl]cyclohexanecarboxamide
项目整合开发状态: Preclinical
项目研究机构: Malesci (Originator), Menarini (Originator)
合成路线:The acylation of 3-(2-naphthyl)-D-alanine (I) with phenylacetyl chloride (II) and bis(trimethylsilyl)acetamide in THF gives the expected N-phenylacetyl derivative (III),which is methylated with NaH and methyl iodide in THF yielding the N-methyl derivative (IV).The reaction of (IV) with 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide (WSC),HOBT and ammonium hydroxide affords the corresponding alaninamide (V),which by reaction with bis(trifluoroacetoxy)iodobenzene (BTI) in acetonitrile is converted into the monoacylated gemdiamine (VI).The condensation of (VI) with cis-2-(1H-indol-3-ylcarboxamido)cyclohexanecarboxylic acid (VII) by means of WSC and HOBT in DMF affords the target compound as a diastereomeric mixture that is separated by preparative RP-HPLC.