ethyl 6-chloro-2-oxo-2H-chromene-3-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】24822

【品名】ethyl 6-chloro-2-oxo-2H-chromene-3-carboxylate

【CA登记号】

【分子式】C₁₂H₉ClO₄

【分子量】252.65376

【元素组成】C 57.05% H 3.59% Cl 14.03% O 25.33%

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：(I)

This compound can be obtained by two related ways: 1) By cyclization of ethyl 6-chlorocoumarin-3-carboxylate (I) and N-methyl-4-piperiodone (II) by means of sodium acetate in refluxing ethanol, followed by a treatment with refluxing concentrated hydrochloric acid. 2) The cyclization of (I) and (II) by means of ammonium acetate in refluxing ethanol, followed by a treatment with cool concentrated hydrochloric acid gives the lactam od the ethyl monoester of 4a-amino-8-chloro-2-methyl-1,2,3,4,4a,10a-hexahydro(10H)-benzopyrano[3,2-c]pyrid-10-ylmalonic acid (III), which is hydrolyzed with KOH in refluxing ethanol-water to give the corresponding free acid (IV). Finally, this compound is decarboxylated by a treatment with NaHCO3 in refluxing water.

参考文献中间体

合成目标

【1】 Baxter, M.G.; Elphick, A.R.; Miller, A.A.; Sawyer, D.A. (Glaxo Wellcome plc); 1,2,4-Triazine derivs., process for preparing such cpds., pharmaceutical compsns. and intermediates utilized for this process. CA 1133938; EP 0021121 .
【2】 Castaner, J.; Prous, J.; Lortalamine. Drugs Fut 1986, 11, 5, 375.

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)	24822	ethyl 6-chloro-2-oxo-2H-chromene-3-carboxylate		C₁₂H₉ClO₄	详情	详情
(II)	10919	1-Methyl-4-piperidone; 1-Methyltetrahydro-4(1H)-pyridinone; N-Methyl-4-piperidone;1-methylpiperidin-4-one	1445-73-4	C₆H₁₁NO	详情	详情
(III)	24824	ethyl (1S,9R,17S)-6-chloro-12-methyl-16-oxo-2-oxa-12,15-diazatetracyclo[7.5.3.0(1,10).0(3,8)]heptadeca-3,5,7-triene-17-carboxylate		C₁₈H₂₁ClN₂O₄	详情	详情
(IV)	24825	(1S,9R,17S)-6-chloro-12-methyl-16-oxo-2-oxa-12,15-diazatetracyclo[7.5.3.0(1,10).0(3,8)]heptadeca-3,5,7-triene-17-carboxylic acid		C₁₆H₁₇ClN₂O₄	详情	详情

Extended Information