MG-2121

Chemical Name: 1-Benzothien-2-ylsulfonamidomethylphosphonic acid 2-fluoro-4-nitrophenyl monoester
CAS No. 318460-01-4
项目整合开发状态: Preclinical
项目研究机构: MethylGene (Originator)
合成路线:The condensation of N-methyl-N-(1-naphthylmethyl)propargylamine (I) with 1-bromo-2-tert-butylacetylene (II) by means of Cu2Cl2 gives N-methyl-N-(1-naphthylmethyl)-6,6-dimethylhept-2,4-diynylamine (III),which is then reduced selectively with diisobutylaluminurn hydride in toluene.

合成路线:By reductocondensation of amino (IV) with 6,6-dimethylhept-2-en-4-ynal (VI) by means of NaBH4 in methanol.

合成路线:The condensation of propenal (VII) with tert-butylacetylene (VIII) by means of butyllithium gives 6,6-dimethylhept-1-en-4-yn-3-ol (IX),which is rearranged with HBr to the allyl isomer 6,6-dimethylhept-2-en-4-yn-1-yl bromide (X).Finally,this compound is condensed with amine (IV) by means of Na2CO3 in DMF.

合成路线:Addition of formaldehyde to benzothiophene-2-sulfonamide (I),followed by condensation with trimethyl phosphite,furnished the dimethyl (sulfonamidomethyl)phosphonate (II).The phosphonate ester function of (II) was then hydrolyzed by means of bromotrimethylsilane,producing phosphonic acid (III).This was finally coupled to 2-fluoro-4-nitrophenol (IV) using trichloroacetonitrile in hot pyridine to afford the title mono-phosphonate ester.