4-(methoxycarbonyl)benzoic acid -Drug Synthesis Database

【结构式】

【分子编号】43361

【品名】4-(methoxycarbonyl)benzoic acid

【CA登记号】1679-64-7

【分子式】C₉H₈O₄

【分子量】180.16012

【元素组成】C 60% H 4.48% O 35.52%

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：(IV)

Treatment of 2,2-dimethylcyclopentanone (I) with tosylmethyl isocyanide and potassium tert-butoxide produced nitrile (II), which was reduced to amine (III) employing LiAlH4 in THF. Coupling of amine (III) with mono-methyl terephthalate (IV) by means of EDC and HOBt gave amide (V). The target oxadiazole system was then obtained by condensation of (V) with N-hydroxypentamidine (VI) in the presence of NaH, and the (S)-enantiomer was isolated by using chiral HPLC.

参考文献中间体

合成目标

【1】 Poss, M.A.; Lloyd, J.; Rovnyak, G.C.; Caulfield, T.J.; Atwal, K.S.; Stein, P.D.; Ahmad, S. (Bristol-Myers Squibb Co.); Benzoic acid derivs. and related cpds. as antiarrhythmic agents. WO 9837068 .

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)	43358	2,2-dimethylcyclopentanone		C₇H₁₂O	详情	详情
(II)	43359	2,2-dimethylcyclopentanecarbonitrile		C₈H₁₃N	详情	详情
(III)	43360	(2,2-dimethylcyclopentyl)methylamine; (2,2-dimethylcyclopentyl)methanamine		C₈H₁₇N	详情	详情
(IV)	43361	4-(methoxycarbonyl)benzoic acid	1679-64-7	C₉H₈O₄	详情	详情
(V)	43362	methyl 4-([[(2,2-dimethylcyclopentyl)methyl]amino]carbonyl)benzoate		C₁₇H₂₃NO₃	详情	详情
(VI)	43363	N'-hydroxypentanimidamide		C₅H₁₂N₂O	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 terephthalic acid monomethyl ester (I) with SOCl2 in dichloromethane gives the acyl chloride (II), which is condensed with 3-(3-ethoxy-4-methoxyphenyl)-1-methylpiperidin-4-amine (III) by means of TEA in dichloromethane, yielding the corresponding amide (IV). The cyclization of (IV) by means of POCl3 in refluxing acetonitrile affords the benzo-naphthyridine (V), which is treated with diisopropylamine in methanol to provide the target diisopropyl carboxamide.

参考文献中间体

合成目标

【1】 Gutterer, B.; Amschler, H.; Ulrich, W.-R.; Martin, T.; Bär, T.; Hatzelmann, A.; Sanders, K.; Beume, R.; Boss, H.; Häfner, D.; Kley, H.-P.; Goebel, K.-J. (Altana Pharma Deutschland GmbH ); Benzonaphthyridines as bronchial therapeutics. EP 0937074; JP 2001503442; US 6008215; WO 9821208 .

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)	43361	4-(methoxycarbonyl)benzoic acid	1679-64-7	C₉H₈O₄	详情	详情
(II)	25029	p-Phthalic acid monomethyl ester chloride; Terephthalic acid monomethyl ester chloride; Methyl 4-chlorocarbonylbenzoate	7377-26-6	C₉H₇ClO₃	详情	详情
(III)	53959	3-(3-ethoxy-4-methoxyphenyl)-1-methyl-4-piperidinamine; 3-(3-ethoxy-4-methoxyphenyl)-1-methyl-4-piperidinylamine	n/a	C₁₅H₂₄N₂O₂	详情	详情
(IV)	53960	methyl 4-({[3-(3-ethoxy-4-methoxyphenyl)-1-methyl-4-piperidinyl]amino}carbonyl)benzoate	n/a	C₂₄H₃₀N₂O₅	详情	详情
(V)	53961	methyl 4-[(4aS,10bR)-9-ethoxy-8-methoxy-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridin-6-yl]benzoate	n/a	C₂₄H₂₈N₂O₄	详情	详情
(VI)	13565	N-Isopropyl-2-propanamine; Bis(isopropyl)amine; N,N-Diisopropylamine	108-18-9	C₆H₁₅N	详情	详情

Extended Information