ethyl isonicotinate -Drug Synthesis Database

【结构式】

【分子编号】43671

【品名】ethyl isonicotinate

【CA登记号】1570-45-2

【分子式】C₈H₉NO₂

【分子量】151.165

【元素组成】C 63.56% H 6% N 9.27% O 21.17%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(I)

The methylation of pyridine-4-carboxylic acid (X) gives the pyridinium iodide (XI), which is reduced with NaBH4 to yield 1-methyl-1,2,3,6-tetrahydropyridine-4-carboxylic acid ethyl ester (XII). The desmethylation of (XII) with ethyl chloroformate (XIII) affords 1,23,6-tetrahydropyridine-1,4-dicarboxylic acid diethyl ester (XIV), which is finally hydrolyzed and monodecarboxylated with HCl and TEA.

参考文献中间体

合成目标

【1】 Christensen, V.; Krogsgaard-Larsen, P.; Falch, E.; Chemistry and pharmacology of the GABA agonists THIP (Gabodaxol) and isoguvacine. Drugs Fut 1984, 9, 8, 597.
【2】 Johnston, G.A.R.; Krogsgaard-Larsen, P.; Structure-activity studies on the inhibition of GABA binding to rat brain membranes by muscinol and related compounds. J Neurochem 1978, 30, 1377-1382.
【3】 Krogsgaard-Larsen, P.; Christensen, T.R.; GABA agonists. Synthesis and structure-activity studies on analogues of isoguvacine and THIP. Eur J Med Chem 1979, 14, 157-164.

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)	43671	ethyl isonicotinate	1570-45-2	C₈H₉NO₂	详情	详情
(II)	43672	4-(ethoxycarbonyl)-1-methylpyridinium iodide		C₉H₁₂INO₂	详情	详情
(III)	43673	ethyl 1-methyl-1,2,3,6-tetrahydro-4-pyridinecarboxylate		C₉H₁₅NO₂	详情	详情
(IV)	11229	1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate	541-41-3	C₃H₅ClO₂	详情	详情
(V)	43674	diethyl 3,6-dihydro-1,4(2H)-pyridinedicarboxylate		C₁₁H₁₇NO₄	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 reaction of pyridine-4-carboxylic acid ethyl ester (I) with methyl iodide gives the pyridinium iodide (II), which is reduced with tritiated NaB3H4, yielding the tritiated tetrahydropyridine (III). The desmethylation of (III) with ethyl chloroformate (IV), followed by a treatment with HBr, affords the tritiated target compound.

参考文献中间体

合成目标

【1】 Christensen, V.; Krogsgaard-Larsen, P.; Falch, E.; Chemistry and pharmacology of the GABA agonists THIP (Gabodaxol) and isoguvacine. Drugs Fut 1984, 9, 8, 597.
【2】 Krogsgaard-Larsen, P.; Christensen, S.B.; Preparations of deuterium labeled guvacine and isoguvacine. J Label Compd Radiopharm 1980, 17, 191-202.

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)	43671	ethyl isonicotinate	1570-45-2	C₈H₉NO₂	详情	详情
(II)	43672	4-(ethoxycarbonyl)-1-methylpyridinium iodide		C₉H₁₂INO₂	详情	详情
(III)	43673	ethyl 1-methyl-1,2,3,6-tetrahydro-4-pyridinecarboxylate		C₉H₁₅NO₂	详情	详情
(IV)	11229	1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate	541-41-3	C₃H₅ClO₂	详情	详情

合成路线3

该中间体在本合成路线中的序号： (I)

参考文献中间体

合成目标

【1】 Daeniker HU, Grob CA. 1964. 3-Quinuclidone hydrochloride. Org Syn, 44: 86～90
【2】 Han XY, Liu H, Liu CH, et al. 2005. Synthesis of the optical rsomers of a new anticholinergic drug, penehyclidine hydrochloride (8018). Bioorg Med Chemm lett, 15(8):1979～1982
【3】 Ji JG, Li T. 2005. Preparatum of bicycloheterocyclyl substituted quiniculidine derivatives for use in pharmaceutical compositions which modulate the effects of α 7 nicotinic acetylcholine receptors(α 7 nAChR). US 2005137184

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)	43671	ethyl isonicotinate	1570-45-2	C₈H₉NO₂	详情	详情
(II)	66741	1-(2-ethoxy-2-oxoethyl)-4-(ethoxycarbonyl)pyridin-1-ium bromide		C₁₂H₁₆BrNO₄	详情	详情
(III)	66742	ethyl 1-(2-ethoxy-2-oxoethyl)piperidine-4-carboxylate	1838-39-7	C₁₂H₂₁NO₄	详情	详情
(IV)	66743	ethyl 3-oxoquinuclidine-2-carboxylate		C₁₀H₁₅NO₃	详情	详情
(V)	66744	quinuclidin-3-one hydrochloride		C₇H₁₁NO.HCl	详情	详情
(VI)	66745	quinuclidin-3-ol		C₇H₁₃NO	详情	详情
(VII)	66746	quinuclidin-3-yl acetate		C₉H₁₅NO₂	详情	详情
(VIII)	16152	(3R)-1-azabicyclo[2.2.2]octan-3-ol; (R)-(-)-Quinuclidinol	42437-96-7	C₇H₁₃NO	详情	详情

Extended Information