NNC-52-0956
Chemical Name: 2-(Oxaloamino)-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylic acid; N-(3-Carboxy-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)oxamic acid
CAS No. 243967-42-2, 243966-09-8 (hydrochloride)
项目整合开发状态: Biological Testing
项目研究机构: Novo Nordisk (Originator), Ontogen (Originator)
合成路线:Knoevenagel condensation between N-Boc-4-piperidinone (I) and ethyl cyanoacetate (II) produced the piperidinylidene cyanoacetate (III),which was further converted to the thienopyridine derivative (IV) upon treatment with sulfur and morpholine.Acylation of amine (IV) with ethyl oxalyl chloride (V) furnished the oxalamide (VI).Subsequent hydrolysis of the ester groups of (VI) under basic conditions led to diacid (VII).The title compound was finally obtained by trifluoroacetic acid-promoted Boc group cleavage.
📌 参考资料/链接：
参考文献标题:Modulators of protein tyrosine phosphatases
文献作者:Jones,T.K.; Jeppesen,L.; Ripka,W.C.; Andersen,H.S.; Olsen,O.H.; Bakir,F.; Branner,S.; Moller,N.P.H.; Jeppesen,C.B.; Richter,L.S.; Vagner,J.; Iversen,L.F.; Holsworth,D.D.; Axe,F.U.; Ge,Y.; et al.(Novo Nordisk A/S; Ontogen Corp.)
参考来源:WO 9946237
📄 详细内容
合成路线:Knoevenagel condensation between N-Boc-4-piperidinone (I) and ethyl cyanoacetate (II) produced the piperidinylidene cyanoacetate (III),which was further converted to the thienopyridine derivative (IV) upon treatment with sulfur and morpholine.Acylation of amine (IV) with ethyl oxalyl chloride (V) furnished the oxalamide (VI).Subsequent hydrolysis of the ester groups of (VI) under basic conditions led to diacid (VII).The title compound was finally obtained by trifluoroacetic acid-promoted Boc group cleavage.
参考文献标题:Modulators of protein tyrosine phosphatases (PTPases)
文献作者:Jones,T.K.; Ripka,W.C.; Andersen,H.S.; Olsen,O.H.; Bakir,F.; Branner,S.; Iversen,L.F.; Holsworth,D.D.; Axe,F.U.; Ge,Y.; Uyeda,R.T.; Judge,L.M.; Moeller,N.P.H.(Novo Nordisk A/S; Ontogen Corp.)
参考来源:JP 2002506072; US 6410586; WO 9946267
产品链接: CAS No. 243967-42-2›› 产品链接: CAS No.243966-09-8››