1H-imidazo[4,5-b]pyridine -Drug Synthesis Database

【结构式】

【分子编号】44867

【品名】1H-imidazo[4,5-b]pyridine

【CA登记号】

【分子式】C₆H₅N₃

【分子量】119.12592

【元素组成】C 60.5% H 4.23% N 35.27%

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：(XVIII)

Intermediate (XIV) can be obtained as follows: Bromination of methyl cinnamate (XV) with Br2 in CH2Cl2 provides 2,3-dibromo-3-phenylpropanoate (XVI), which is then converted into alpha-bromocinnamic ester (XVII) by reaction with Et3N in refluxing toluene. Treatment of (XVII) with imidazopyridine (XVIII) and NaH in DMF affords derivative (XIX), which is then hydrolyzed by treatment with NaOH in MeOH to furnish carboxylic acid (XX). Finally, (XX) reacts with carbonylditriazole in DMF to give the target intermediate (XIV).

参考文献中间体

合成目标

【1】 Hemmerle, H.; Schubert, G.; Burger, H.-J.; Herling, A.; Efendic, S. (Aventis SA); Cyclohexane derivs., processes for their preparation and their use as glucose-6-phosphatase inhibitors. CA 2149007; CA 4416433; EP 0682024; JP 1995330767; US 5739147 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIV)	44863			C₁₇H₁₂N₆O	详情	详情
(XV)	23888	methyl (E)-3-phenyl-2-propenoate	103-26-4	C₁₀H₁₀O₂	详情	详情
(XVI)	44865	methyl 2,3-dibromo-3-phenylpropanoate		C₁₀H₁₀Br₂O₂	详情	详情
(XVII)	44866	methyl (Z)-2-bromo-3-phenyl-2-propenoate		C₁₀H₉BrO₂	详情	详情
(XVIII)	44867	1H-imidazo[4,5-b]pyridine		C₆H₅N₃	详情	详情
(XIX)	44868	methyl (Z)-3-(1H-imidazo[4,5-b]pyridin-1-yl)-3-phenyl-2-propenoate		C₁₆H₁₃N₃O₂	详情	详情
(XX)	44869	(Z)-3-(1H-imidazo[4,5-b]pyridin-1-yl)-3-phenyl-2-propenoic acid		C₁₅H₁₁N₃O₂	详情	详情
(XXI)	44870	di(1H-1,2,4-triazol-1-yl)methanone		C₅H₄N₆O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The intermediate 1-substituted imidazopyridine (III) was prepared by several procedures. Alkylation of imidazo[4,5-b]pyridine (I) with mesylate (II) in the presence of NaH provided a mixture of the desired compound (III) and its 3-substituted regioisomer (IV), which were separated by column chromatography.

参考文献中间体

合成目标

【1】 Itani, H.; et al.; S-3578, a new broad spectrum parenteral cephalosporin exhibiting potent activity against both methicillin-resistant Staphylococcus aureus (MRSA) and Pseudomonas aeruginosa synthesis and structure-activity relationships. 22nd Symp Med Chem (Nov 27 2002, Shizuoka) 2002, Abst 1P-16.
【2】 Miwa, H.; Yoshida, T.; Shimada, J.; Kuwahara, S.; Nishitani, Y.; S-3578, a new broad-spectrum cephalosporin: I. Synthesis and structure-activity relationships. 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-370.
【3】 Itani, H.; Nishitani, Y.; Irie, T. (Shionogi & Co. Ltd.); Imidazo[4,5-b]pyridiniummethyl-containing cephem cpds. having broad antibacterial spectrum. EP 1134222; WO 0032606 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	44867	1H-imidazo[4,5-b]pyridine	C₆H₅N₃	详情	详情
(II)	54813	3-[(tert-butoxycarbonyl)(methyl)amino]propyl methanesulfonate	C₁₀H₂₁NO₅S	详情	详情
(III)	54814	tert-butyl 3-(1H-imidazo[4,5-b]pyridin-1-yl)propyl(methyl)carbamate	C₁₅H₂₂N₄O₂	详情	详情
(IV)	54815	tert-butyl 3-(3H-imidazo[4,5-b]pyridin-3-yl)propyl(methyl)carbamate	C₁₅H₂₂N₄O₂	详情	详情

Extended Information