MRS-1505

2-(3-氯苯基)-4,6-二乙基-5-(丙基磺酰羰基)吡啶-3-羧酸丙酯Chemical Name: 2-(3-Chlorophenyl)-4,6-diethyl-5-(propylsulfanylcarbonyl)pyridine-3-carboxylic acid propyl ester
CAS No. 212329-38-9
项目整合开发状态: Biological Testing
项目研究机构: National Institutes of Health (Originator)
合成路线:Acylation of Meldrum's acid (I) with propionyl chloride (II) in the presence of pyridine gave propionyl derivative (III).Subsequent ring opening of (III) with ethanethiol (IV),followed by decarboxylation provided S-ethyl 3-oxothiovalerate (V).Propyl 3-amino-3-phenyl-2-propenoate (VII) was prepared by reaction of benzoylacetate (VI) with ammonium acetate in refluxing ethanol.Then,Hantzsch condensation of ketothioester (V),beta-enaminoester (VII),and butyraldehyde (VIII) in EtOH at 80 C in a sealed tube furnished the dihydropyridine (IX).Finally,oxidation of (IX) using chloranil (X) in boiling THF gave the target pyridine.

合成路线:Acylation of Meldrum's acid (I) with propionyl chloride (II) in the presence of pyridine gave propionyl derivative (III).Subsequent ring opening of (III) with ethanethiol (IV),followed by decarboxylation provided S-ethyl 3-oxothiovalerate (V).Ethyl 3-amino-3-phenyl-2-propenoate (VII) was prepared by reaction of benzoylacetate (VI) with ammonium acetate in refluxing ethanol.Then,Hantzsch condensation of ketothioester (V),beta-enaminoester (VII),and propionaldehyde (VIII) in EtOH at 80 C in a sealed tube furnished the dihydropyridine (IX).Finally,oxidation of (IX) using chloranil (X) in boiling THF gave the target pyridine.

合成路线:Acylation of Meldrum's acid (I) with propionyl chloride (II) in the presence of pyridine gave propionyl derivative (III).Subsequent ring opening of (III) with propanethiol (IV),followed by decarboxylation provided S-propyl 3-oxothiovalerate (V).Propyl 3-amino-3-(m-chlorophenyl)-2-propenoate (VII) was prepared by reaction of (3-chlorobenzoyl)acetate (VI) with ammonium acetate in refluxing ethanol.Then,Hantzsch condensation of ketothioester (V),beta-enaminoester (VII),and propionaldehyde (VIII) in EtOH at 80 C in a sealed tube furnished the dihydropyridine (IX).Finally,oxidation of (IX) using chloranil (X) in boiling THF gave the target pyridine.

合成路线:Acylation of Meldrum's acid (I) with butyryl chloride (II) in the presence of pyridine gave butyryl derivative (III).Subsequent ring opening of (III) with ethanethiol (IV),followed by decarboxylation provided S-ethyl 3-oxothiocaproate (V).Ethyl 3-amino-3-phenyl-2-propenoate (VII) was prepared by reaction of benzoylacetate (VI) with ammonium acetate in refluxing ethanol.Then,Hantzsch condensation of ketothioester (V),b-enaminoester (VII),and propionaldehyde (VIII) in EtOH at 80 C in a sealed tube furnished the dihydropyridine (IX).Finally,oxidation of (IX) using chloranil (X) in boiling THF gave the target pyridine.