Amrinone, Win-40680, Cordarex, Amcoral, Cartonic, Wincoram, Inocor(lactate)

氨力农Chemical Name: 5-Amino-(3,4'-bipyridin)-6(1H)-one; 3-Amino-5-(4-pyridinyl)-2(1H)pyridinone
CAS No. 60719-84-8
项目整合开发状态: Launched-1983
项目研究机构: Sanofi-Aventis (Originator), Yamanouchi (Licensee)
合成路线:Compound can be prepared in several different ways:1) The condensation of 2-(4-pyridinyl)-3-dimethylaminoacrolein (I) with cyanacetamide (II) by means of sodium methoxide in refluxing methanol gives 1,2-dihydro-5-(4-pyridinyl)-2-oxonicotinonitrile (III),which by hydrolysis with 90% H2SO4 at 100 C is converted into 1,2-dihydro-5-(4-pyridinyl)-2-oxonicotinamide (IV).Finally,this compound is submitted to a Hofmann degradation with Br2 and NaOH in water.2) Compound (III) can also be obtained by condensation of 2-(4-pyridinyl)-malonodialdehyde (V) with cyanacetamide (II) by means of morpholine and acetic acid in refluxing benzene.3) The hydrolysis of (III) with refluxing 50% H2SO4 gives 1,2-dihydro-5-(4-pyridinyl)-2-oxonicotinic acid (VI),which by reaction with 90% HNO3 in conc.H2SO4 at 80 C yields 3-nitro-5-(4-pyridinyl)-2(1H)-pyridinone (VII).Finally,this compound is reduced with H2 over Pd/C in DMF.4) The decarboxylative hydrolysis of (III) with refluxing 80% H2SO4 gives 5-(4-pyridinyl)-2(1H)-pyridinone (VIII),which can be nitrated with conc.HNO3 in H2SO4 at 80 C to give also (VII).