ethyl 3-methoxybenzenecarboximidoate -Drug Synthesis Database

【结构式】

【分子编号】34363

【品名】ethyl 3-methoxybenzenecarboximidoate

【CA登记号】

【分子式】C₁₀H₁₃NO₂

【分子量】179.21876

【元素组成】C 67.02% H 7.31% N 7.82% O 17.85%

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 condensation of ethyl 3-metboxybenzimidate (I) with 2-ethybenzoic hydrazide (II) in refluxing CH2Cl2 gives the benzoylamidrazone (III), which is then cyclized by means of K2CO3 in refluxing 2-etoxyethanol.

参考文献中间体

合成目标

【1】 Omodei-Salé, A.; Galliani, G.; Consonni, P.; A new class of nonhormonal pregnancy-terminating agents. Synthesis and contragestational activity of 3,5-diaryl-s-triazoles. J Med Chem 1983, 26, 8, 1187-92.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	34363	ethyl 3-methoxybenzenecarboximidoate	C₁₀H₁₃NO₂	详情	详情
(II)	34364	2-ethylbenzohydrazide	C₉H₁₂N₂O	详情	详情
(III)	34365	N'-(2-ethylbenzoyl)-3-methoxybenzenecarbohydrazonamide	C₁₇H₁₉N₃O₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

By cyclization of ethyl m-methoxybenzimidate (I) with 2-ethylbenzoyl hydrazide (II) at 125 C.

参考文献中间体

合成目标

【1】 Omodei Sale, A.; Consonni, P.; Galliani, G.; Lerner, L. (Lepetit SpA); 3,5-Disubstd.-1H-1,2,4-triazoles. DE 2819372 .
【2】 Hillier, K.; Blancafort, P.; Castaner, J.; Serradell, M.N.; DL-111-IT. Drugs Fut 1982, 7, 12, 875.

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)	34364	2-ethylbenzohydrazide		C₉H₁₂N₂O	详情	详情
(II)	34363	ethyl 3-methoxybenzenecarboximidoate		C₁₀H₁₃NO₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(II)

3-Methoxybenzonitrile (I) was converted to the corresponding imidate (II) by treatment with ethanolic HCl. Condensation of (II) with aminoacetaldehyde diethyl acetal (III) gave amidine (IV), which was cyclized with diethyl ethoxymethylenemalonate (V) in refluxing ethanol to yield the pyrimidinone (VI). Hydrolysis of the ethyl ester function of (VI) by treatment with LiI in hot pyridine provided acid (VII). This was subjected to a Curtius rearrangement with diphenylphosphoryl azide, and the intermediate isocyanate was condensed with benzyl alcohol to produce the benzyl carbamate (VIII). Acid hydrolysis of the diethyl acetal group of (VIII), followed by oxidation of the resulting aldehyde with sodium chlorite, furnished the carboxylic acid (IX).

参考文献中间体

合成目标

【1】 Akahoshi, F.; Ashimori, A.; Yoshimura, T.; Eda, M.; Sakashita, H.; Nakajima, M.; Imada, T. (Welfide Corporation); Novel heterocyclic amide cpds. and medicinal uses thereof. EP 0940400; US 6080738; WO 9818794 .

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)	36250	3-methoxybenzonitrile	1527-89-5	C₈H₇NO	详情	详情
(II)	34363	ethyl 3-methoxybenzenecarboximidoate		C₁₀H₁₃NO₂	详情	详情
(III)	10331	2,2-Diethoxy-1-ethanamine; 2,2-Diethoxyethylamine; Aminoacetaldehyde diethyl acetal	645-36-3	C₆H₁₅NO₂	详情	详情
(IV)	48623	N-(2,2-diethoxyethyl)-3-methoxybenzenecarboximidamide		C₁₄H₂₂N₂O₃	详情	详情
(V)	14088	Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate	87-13-8	C₁₀H₁₆O₅	详情	详情
(VI)	48624	ethyl 1-(2,2-diethoxyethyl)-2-(3-methoxyphenyl)-6-oxo-1,6-dihydro-5-pyrimidinecarboxylate		C₂₀H₂₆N₂O₆	详情	详情
(VII)	48625	1-(2,2-diethoxyethyl)-2-(3-methoxyphenyl)-6-oxo-1,6-dihydro-5-pyrimidinecarboxylic acid		C₁₈H₂₂N₂O₆	详情	详情
(VIII)	48626	benzyl 1-(2,2-diethoxyethyl)-2-(3-methoxyphenyl)-6-oxo-1,6-dihydro-5-pyrimidinylcarbamate		C₂₅H₂₉N₃O₆	详情	详情
(IX)	48627	2-[5-[[(benzyloxy)carbonyl]amino]-2-(3-methoxyphenyl)-6-oxo-1(6H)-pyrimidinyl]acetic acid		C₂₁H₁₉N₃O₆	详情	详情

Extended Information