NNC-57-0545
Chemical Name: 1-[4-Amino-2-(phenylamino)thiazol-5-yl]-(3-pyridyl)methanone
项目整合开发状态: Biological Testing
项目研究机构: Novo Nordisk (Originator)
合成路线:The reaction of N1-amidino-N3-phenylthiourea (I) with 2-bromo-1-cyclopropylethanone (II) in ethanol/acetone gives the N1-amidino-S-(2-cyclopropyl-2-oxoethyl)-N3-phenylisothiourea (III),which without isolation is cyclized to the target aminothiazole by means of TEA.
合成路线:The reaction of aniline (I) with di(2-pyridyl)thione (DPT) gives the corresponding isothiocyanate (II),which is condensed with cyanamide (III) and 2-bromo-1-cyclopropylethanone (IV) (obtained by bromination of acetylcyclopropane (V)) by means of NaOMe to yield the adduct (VI).This compound,without isolation,cyclizes to the target thiazole.
合成路线:The reaction of N1-amidino-N3-propylthiourea (I) with 2-bromo-1-(3-pyridyl)ethanone (II) in ethanol/acetone gives the N1-amidino-S-[2-oxo-2-(3-pyridyl)ethyl]-N3-propylisothiourea (III),which without isolation is cyclized to the target aminothiazole by means of TEA.
合成路线:The reaction of N1-amidino-N3-phenylthiourea (I) with 2-bromo-1-(3-pyridyl)ethanone (II) in ethanol/acetone gives the N1-amidino-S-[2-oxo-2-(3-pyridyl)ethyl]-N3-phenylisothiourea (III),which without isolation is cyclized to the target aminothiazole by means of TEA.
合成路线:The reaction of N1-amidino-N3-phenylthiourea (I) with 3-(benzyloxy)phenacyl bromide (II) in ethanol/acetone gives the N1-amidino-S-[2-(3-benzyloxyphenyl)-2-oxoethyl]-N3-phenylisothiourea (III),which without isolation is cyclized to the target aminothiazole by means of TEA.
合成路线:The reaction of aniline (I) with di(2-pyridyl)thione (DPT) gives the corresponding isothiocyanate (II),which is condensed with cyanamide (III) and 2-bromo-1-(3-benzyloxyphenyl)ethanone (IV) by means of NaOMe to yield the adduct (V).This compound,without isolation,cyclizes to the target thiazole.
📌 参考资料/链接：
参考文献标题:2,4-Diaminothiazole derivs.
文献作者:Olesen,P.H.; Kurtzhals,P.; Bowler,A.N.; Soerensen,A.R.; Worsaae,H.; Hansen,B.F.(Novo Nordisk A/S)
参考来源:WO 0156567
📄 详细内容
合成路线:The reaction of N1-amidino-N3-phenylthiourea (I) with 2-bromo-1-cyclopropylethanone (II) in ethanol/acetone gives the N1-amidino-S-(2-cyclopropyl-2-oxoethyl)-N3-phenylisothiourea (III),which without isolation is cyclized to the target aminothiazole by means of TEA.
合成路线:The reaction of aniline (I) with di(2-pyridyl)thione (DPT) gives the corresponding isothiocyanate (II),which is condensed with cyanamide (III) and 2-bromo-1-cyclopropylethanone (IV) (obtained by bromination of acetylcyclopropane (V)) by means of NaOMe to yield the adduct (VI).This compound,without isolation,cyclizes to the target thiazole.
合成路线:The reaction of N1-amidino-N3-propylthiourea (I) with 2-bromo-1-(3-pyridyl)ethanone (II) in ethanol/acetone gives the N1-amidino-S-[2-oxo-2-(3-pyridyl)ethyl]-N3-propylisothiourea (III),which without isolation is cyclized to the target aminothiazole by means of TEA.
合成路线:The reaction of propylamine (I) with di(2-pyridyl)thione (DPT) gives the corresponding isothiocyanate (II),which is condensed with cyanamide (III) and 2-bromo-1-(3-pyridyl)ethanone (IV) by means of NaOMe to yield the adduct (V).This compound,without isolation,cyclizes to the target thiazole.
合成路线:The reaction of N1-amidino-N3-phenylthiourea (I) with 2-bromo-1-(3-pyridyl)ethanone (II) in ethanol/acetone gives the N1-amidino-S-[2-oxo-2-(3-pyridyl)ethyl]-N3-phenylisothiourea (III),which without isolation is cyclized to the target aminothiazole by means of TEA.
合成路线:The reaction of aniline (I) with di(2-pyridyl)thione (DPT) gives the corresponding isothiocyanate (II),which is condensed with cyanamide (III) and 2-bromo-1-(3-pyridyl)ethanone (IV) by means of NaOMe to yield the adduct (V).This compound,without isolation,cyclizes to the target thiazole.
合成路线:The reaction of N1-amidino-N3-phenylthiourea (I) with 3-(benzyloxy)phenacyl bromide (II) in ethanol/acetone gives the N1-amidino-S-[2-(3-benzyloxyphenyl)-2-oxoethyl]-N3-phenylisothiourea (III),which without isolation is cyclized to the target aminothiazole by means of TEA.
参考文献标题:2,4-Diaminothiazoles: A novel class of glycogen synthase kinase-3 (GSK-3) inhibitors
文献作者:Sorensen,A.R.; Engelhardt,S.; Kurtzhals,P.; Urso,B.; Bowler,A.N.
参考来源:11th RSC-SCI Med Chem Symp (Sept 9 2001,Cambridge) 2001,Abst P20