1-{[2-oxo-1(2H)-pyridinyl]carbothioyl}-2(1H)-pyridinone -Drug Synthesis Database

【结构式】

【分子编号】61696

【品名】1-{[2-oxo-1(2H)-pyridinyl]carbothioyl}-2(1H)-pyridinone

【CA登记号】

【分子式】C₁₁H₈N₂O₂S

【分子量】232.2628

【元素组成】C 56.88% H 3.47% N 12.06% O 13.78% S 13.81%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VI)

Intermediate (VII) is prepared by the following route. Oxidation of 2-methoxy-4-nitrotoluene (I) by means of chromic acid in the presence of Ac2O affords acylal (II), which is further hydrolyzed to aldehyde (III) under acidic conditions. Treatment of benzaldehyde (III) with TOSMIC reagent in the presence of K2CO3 gives rise to the phenyl oxazole derivative (IV). Nitro group reduction in (IV) with H2 and Pd/C yields aniline (V). This is then converted into isothiocyanate (VII) employing 1,1'-thiocarbonyldi-2(2H)-pyridone (VI).

参考文献中间体

合成目标

【1】 Liu, C.; Leftheris, K.; Pitts, W.J.; Iwanowicz, E.J.; Dhar, T.G.M.; Gu, H.H. (Bristol-Myers Squibb Co.); Cpds. derived from an amine nucleus that are inhibitors of IMPDH enzyme. EP 1126843; US 6399773; WO 0025780 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	39654	methyl 2-methyl-5-nitrophenyl ether; 2-methoxy-1-methyl-4-nitrobenzene	13120-77-9	C₈H₉NO₃	详情	详情
(II)	39655	(acetoxy)(2-methoxy-4-nitrophenyl)methyl acetate		C₁₂H₁₃NO₇	详情	详情
(III)	39656	2-methoxy-4-nitrobenzaldehyde		C₈H₇NO₄	详情	详情
(IV)	39657	methyl 5-nitro-2-(1,3-oxazol-5-yl)phenyl ether; 5-(2-methoxy-4-nitrophenyl)-1,3-oxazole		C₁₀H₈N₂O₄	详情	详情
(V)	39658			C₁₀H₁₀N₂O₂	详情	详情
(VI)	61696	1-{[2-oxo-1(2H)-pyridinyl]carbothioyl}-2(1H)-pyridinone		C₁₁H₈N₂O₂S	详情	详情
(VII)	61697	3-methoxy-4-(1,3-oxazol-5-yl)phenyl isothiocyanate; 5-(4-isothiocyanato-2-methoxyphenyl)-1,3-oxazole		C₁₁H₈N₂O₂S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

Treatment of 6-aminoisoquinoline (I) with 1,1'-thiocarbonyldi-2(1H)-pyridone (II) provides the isothiocyanate (III). Subsequent condensation of (III) with 2-azidoacetophenone (IV) in the presence of triphenylphosphine affords the title oxazole derivative.

参考文献中间体

合成目标

【1】 Chen, P.; Norris, D.; Haslow, K.D.; Dhar, T.G.M.; Pitts, W.J.; Watterson, S.H.; Cheney, D.L.; Bassolino, D.A.; Fleener, C.A.; Rouleau, K.A.; Hollenbaugh, D.L.; Townsend, R.M.; Barrish, J.C.; Iwanowicz, E.J.; Identification of novel and potent isoquinoline aminooxazole-based IMPDH inhibitors. Bioorg Med Chem Lett 2003, 13, 7, 1345.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	64245	6-isoquinolinamine; 6-isoquinolinylamine	C₉H₈N₂	详情	详情
(II)	61696	1-{[2-oxo-1(2H)-pyridinyl]carbothioyl}-2(1H)-pyridinone	C₁₁H₈N₂O₂S	详情	详情
(III)	64246	6-isothiocyanatoisoquinoline; 6-isoquinolinyl isothiocyanate	C₁₀H₆N₂S	详情	详情
(IV)	26720	2-azido-1-phenyl-1-ethanone	C₈H₇N₃O	详情	详情

Extended Information