6,7,8,9-tetrahydropyrido[3',2':4,5]imidazo[1,2-a]pyridin-6-ol -Drug Synthesis Database

【结构式】

【分子编号】35471

【品名】6,7,8,9-tetrahydropyrido[3',2':4,5]imidazo[1,2-a]pyridin-6-ol

【CA登记号】

【分子式】C₁₀H₁₁N₃O

【分子量】189.21696

【元素组成】C 63.48% H 5.86% N 22.21% O 8.46%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(V)

The reaction of 2-chloro-3-nitropyridine (I) with piperidine (II) in dichloromethane gives 3-nitro-2-(1-piperidinyl)pyridine (III), which is cyclized by means of anhydrous ZnCl2 in refluxing acetic acid yielding the acetoxy dipyridoimidazole (IV). The deacetylation of (IV) with NaOH in methanol affords the alcohol (V), which is oxidized with oxalyl chloride and DMSO in dichloromethane to give the ketone (VI). The bromination of (VI) with Br2 in hot aqueous HBr yields the alpha-bromoketone (VII), which is finally cyclized with N,N-dimethylthiourea (VIII) in refluxing ethanol.

参考文献中间体

合成目标

【1】 Chang, M.S.; Chung, K.J.; Park, S.H.; Kim, Y.H.; Kim, K.B.; Choi, W.S.; Kim, S.G.; Lee, J.M.; Seo, K.H.; Yoo, H.Y.; Paek, J.H.; Kang, D.P. (Yung-Jin Pharmaceutical Co., Ltd.); Benz- or pyrido-imidazole derivs.. WO 9703077 .

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)	10321	2-Chloro-3-nitropyridine	5470-18-8	C₅H₃ClN₂O₂	详情	详情
(II)	10158	Piperidine	110-89-4	C₅H₁₁N	详情	详情
(III)	35469	3-nitro-2-(1-piperidinyl)pyridine		C₁₀H₁₃N₃O₂	详情	详情
(IV)	35470	6,7,8,9-tetrahydropyrido[3',2':4,5]imidazo[1,2-a]pyridin-6-yl acetate		C₁₂H₁₃N₃O₂	详情	详情
(V)	35471	6,7,8,9-tetrahydropyrido[3',2':4,5]imidazo[1,2-a]pyridin-6-ol		C₁₀H₁₁N₃O	详情	详情
(VI)	35472	8,9-dihydropyrido[3',2':4,5]imidazo[1,2-a]pyridin-6(7H)-one		C₁₀H₉N₃O	详情	详情
(VII)	35473	7-bromo-8,9-dihydropyrido[3',2':4,5]imidazo[1,2-a]pyridin-6(7H)-one		C₁₀H₈BrN₃O	详情	详情
(VIII)	35474	N,N-dimethylthiourea		C₃H₈N₂S	详情	详情

Extended Information