SMP-500

Chemical Name: N-[1-Butyl-2-oxo-4-[3-(pyridin-3-ylmethoxy)phenyl]-1,2-dihydro-1,8-naphthyridin-3-yl]-N'-(2,6-diisopropylphenyl)urea nitrate
CAS No. 208166-87-4 (free base)
项目整合开发状态: Preclinical
项目研究机构: Sumitomo Pharmaceuticals (Originator)
合成路线:Condensation of 2-amino-3-(3-methoxybenzoyl)pyridine (I) with diethyl malonate in refluxing pyridine provides the naphthyridine derivative (II),which is subsequently alkylated by butyl iodide in the presence of NaH to afford the N-butyl naphthyridinone (III).Alkaline hydrolysis of the ethyl ester group of (III) leads to the carboxylic acid (IV).This is then subjected to Curtius rearrangement in the presence of diphenylphosphoryl azide,and the obtained isocyanate (V) is further condensed with 2,6-diisopropylaniline (VI) producing urea (VII).

合成路线:Cleavage of the methyl ether function of (VII) by means of BBr3 in cold CH2Cl2 leads to phenol (VIII).This is finally alkylated by 3-picolyl chloride (IX) in the presence of K2CO3/NaI to furnish the title compound.