methyl 3,4-dimethoxy-2-pyridinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】14039

【品名】methyl 3,4-dimethoxy-2-pyridinecarboxylate

【CA登记号】

【分子式】C₉H₁₁NO₄

【分子量】197.19068

【元素组成】C 54.82% H 5.62% N 7.1% O 32.45%

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：(VII)

Using [14C]-labeled (IV) in the preceding synthesis, pantoprazole labeled in the methylene was obtained. Intermediate (IV) labeled in the methylene attached to the pyridine ring can be prepared as follows: The reaction of 2-bromo-3,4-dimethoxypyridine (V) with [14C]-labeled CuCN gives 3,4-dimethoxypyridine-2-carbonitrile (VI), which is hydrolyzed with NaOH and methylated with diazomethane to the methyl ester (VII). Finally, this compound is reduced with LiAlH4 to the corresponding alcohol and treated with SOCl2 to give the chloromethylpyridine (IV*) with the [14C] label. Then this compound is condensed with benzimidazole (III) as usual.

参考文献中间体

合成目标

【1】 Saunders, D.; Lawrie, K.W.M.; Crowe, A.M.; Johnston, C.E.A.; The synthesis of [14C]pantoprazole - SK&F 96022Z - An H+/K+ ATP inhibitor. J Label Compd Radiopharm 1992, 31, 5, 409.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	14035	2-(Chloromethyl)-3,4-dimethoxypyridine; 2-(Chloromethyl)-3-methoxy-4-pyridinyl methyl ether	72830-09-2	C₈H₁₀ClNO₂	详情	详情
(IV)	45195	2-(chloromethyl)-3-methoxy-4-pyridinyl methyl ether; 2-(chloromethyl)-3,4-dimethoxypyridine		C₈H₁₀ClNO₂	详情	详情
(V)	14037	2-Bromo-3-methoxy-4-pyridinyl methyl ether; 2-Bromo-3,4-dimethoxypyridine		C₇H₈BrNO₂	详情	详情
(VI)	14038	3,4-Dimethoxy-2-pyridinecarbonitrile		C₈H₈N₂O₂	详情	详情
(VI)	45193	3,4-dimethoxy-2-pyridinecarbonitrile		C₈H₈N₂O₂	详情	详情
(VII)	14039	methyl 3,4-dimethoxy-2-pyridinecarboxylate		C₉H₁₁NO₄	详情	详情
(VII)	45194	methyl 3,4-dimethoxy-2-pyridinecarboxylate		C₉H₁₁NO₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XVIII)

A related method for the preparation of the intermediate 3,4-dimethoxy-2-(hydroxymethyl)pyridine (XII) has been disclosed. 3-Methoxypyridine (XV) was chlorinated to (XVI) by refluxing in SOCl2. Radical carboxylation of pyridine (XVI) was carried out by reaction with ethyl pyruvate in the presence of hydrogen peroxide and iron(II) sulfate. The resultant ethyl 4-chloro-3-methoxypicolinate (XVII) was then converted to the dimethoxypicolinate (XVIII) by treatment with sodium methoxide. Then, ester group reduction in (XVIII) by means of DIBAL provided the target hydroxymethyl pyridine (XII).

参考文献中间体

合成目标

【1】 Chen, L.; Zoghbi, M. (PDi-Research Laboratories, Inc. ); Synthesis of pharmaceutically useful pyridine derivs.. WO 9850361 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XII)	56501	(3,4-dimethoxy-2-pyridinyl)methanol		C₈H₁₁NO₃	详情	详情
(XV)	56502	3-Methoxypyridine	7295-76-3	C₆H₇NO	详情	详情
(XVI)	56503	4-chloro-3-methoxypyridine; 4-chloro-3-pyridinyl methyl ether		C₆H₆ClNO	详情	详情
(XVII)	56504	ethyl 4-chloro-3-methoxy-2-pyridinecarboxylate		C₉H₁₀ClNO₃	详情	详情
(XVIII)	14039	methyl 3,4-dimethoxy-2-pyridinecarboxylate		C₉H₁₁NO₄	详情	详情

Extended Information