methyl 10-(methyloxy)-5H-dibenzo[b,f]azepine-5-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】52659

【品名】methyl 10-(methyloxy)-5H-dibenzo[b,f]azepine-5-carboxylate

【CA登记号】

【分子式】C₁₇H₁₅NO₃

【分子量】281.31104

【元素组成】C 72.58% H 5.37% N 4.98% O 17.06%

与该中间体有关的原料药合成路线共 4 条

合成路线1 合成路线2 合成路线3 合成路线4

合成路线1

该中间体在本合成路线中的序号：(V)

A new process for the preparation of oxcarbamazepine has been reported: Reaction of 1-phenyl-2,3-dihydro-1H-indol-2-one (I) with NaOH in refluxing THF gives 2-[2-(phenylamino)phenyl]acetic acid (II), which is condensed with dimethyl carbonate (III) by means of butyl lithium in the same solvent to yield 2-[2-[N-(methoxycarbonyl)-N-phenylamino]phenyl]acetic acid (IV). Cyclization of compound (IV) by means of polyphosphoric acid (PPA) at 100 C, followed by treatment of the reaction mixture with hot methanol (65 C) affords 10-methoxy-5H-dibenzo[b,f]azepine-5-carboxylic acid methyl ester (V), which is treated with NaOH in polyethyleneglycol at 100 C to provide 10-methoxy-5H-dibenzo[b,f]azepine (VI). Reaction of (VI) with sodium cyanate in acetic acid gives 10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide (VII), which is finally treated with H2SO4.

参考文献中间体

合成目标

【1】 Kaufmann, D.; Lohse, O.; Zaugg, W.; Funfschilling, P.; Beutler, U. (Novartis AG; Novartis-Erfindungen VmbH); Dibenzo [b,f]azepine derivs. and their preparation. WO 0156992 .

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)	52656	1-phenyl-1,3-dihydro-2H-indol-2-one		C₁₄H₁₁NO	详情	详情
(II)	52657	2-[2-(phenylamino)phenyl]acetic acid		C₁₄H₁₃NO₂	详情	详情
(III)	34197	dimethyl carbonate	616-38-6	C₃H₆O₃	详情	详情
(IV)	52658	2-{2-[[(methyloxy)carbonyl](phenyl)amino]phenyl}acetic acid		C₁₆H₁₅NO₄	详情	详情
(V)	52659	methyl 10-(methyloxy)-5H-dibenzo[b,f]azepine-5-carboxylate		C₁₇H₁₅NO₃	详情	详情
(VI)	24333	10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene	4698-11-7	C₁₅H₁₃NO	详情	详情
(VII)	24335	10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide		C₁₆H₁₄N₂O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

参考文献中间体

合成目标

【1】 Fuenfschilling PC, Zang W, Beutler U et al. 2005.A new Industrial Process for Oxcarbazepine. Org.Proc. Res. Dev.,9:272-277.

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)	69514	2-(2-(2-methoxy-2-oxo-1-phenylethyl)phenyl)acetic acid		C₁₇H₁₆O₄	详情	详情
(II)	69515	methyl 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxylate		C₁₆H₁₃NO₃	详情	详情
(III)	52659	methyl 10-(methyloxy)-5H-dibenzo[b,f]azepine-5-carboxylate		C₁₇H₁₅NO₃	详情	详情
(IV)	24333	10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene	4698-11-7	C₁₅H₁₃NO	详情	详情
(V)	24335	10-methoxy-5H-dibenzo[b,f]azepine-5-carboxamide		C₁₆H₁₄N₂O₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(III)

参考文献中间体

合成目标

【1】 Kaufmann D, Fuenfschilling PC,Beutler U, et al.2004.A new synthesis of oxcarbazepine using a friedelcrafts cyclization strategy. Tetrahedron Lett,45:5275-5278.

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)	52658	2-{2-[[(methyloxy)carbonyl](phenyl)amino]phenyl}acetic acid		C₁₆H₁₅NO₄	详情	详情
(II)	69515	methyl 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxylate		C₁₆H₁₃NO₃	详情	详情
(III)	52659	methyl 10-(methyloxy)-5H-dibenzo[b,f]azepine-5-carboxylate		C₁₇H₁₅NO₃	详情	详情
(IV)	24333	10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene	4698-11-7	C₁₅H₁₃NO	详情	详情

合成路线4

该中间体在本合成路线中的序号：(V)

参考文献中间体

合成目标

【1】 Fuenfschilling P, Kaufmann D, Lohse O, et al.2001.Preparation of dibenzo[b,f] azepine derivatives. WO 2001056992.

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)	69531	2-(o-tolylamino)benzoic acid；2-(2-Methylanilino)benzoic acid;N-(2-Methylphenyl)anthranilic acid;N-(2-Tolyl)anthranilic acid;N-(o-Tolyl)anthranilic acid；N-(o-Methylphenyl)anthranilic acid; N-(2'-Methylphenyl)anthranilic acid;	16610-44-9	C₁₄H₁₃NO₂	详情	详情
(II)	69532	N,N-dimethyl-2-(o-tolylamino)benzamide		C₁₆H₁₈N₂O	详情	详情
(III)	69533	methyl (2-(dimethylcarbamoyl)phenyl)(o-tolyl)carbamate		C₁₈H₂₀N₂O₃	详情	详情
(IV)	69515	methyl 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxylate		C₁₆H₁₃NO₃	详情	详情
(V)	52659	methyl 10-(methyloxy)-5H-dibenzo[b,f]azepine-5-carboxylate		C₁₇H₁₅NO₃	详情	详情
(VI)	24333	10-methoxy-5H-dibenzo[b,f]azepine;10-Methoxyiminostilbene	4698-11-7	C₁₅H₁₃NO	详情	详情

Extended Information