4-[2-(aminocarbonyl)-4-pyridinyl]benzoic acid -Drug Synthesis Database

【结构式】

【分子编号】46461

【品名】4-[2-(aminocarbonyl)-4-pyridinyl]benzoic acid

【CA登记号】

【分子式】C₁₃H₁₀N₂O₃

【分子量】242.23408

【元素组成】C 64.46% H 4.16% N 11.56% O 19.81%

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：(III)

The intermediate pyridylbenzoic acid (III) was prepared by treatment of pyridine-N-oxide (I) with trimethylsilyl cyanide, followed by acid hydrolysis of the cyano and ester groups

参考文献中间体

合成目标

【1】 Pauls, H.W.; Brown, K.D.; Liang, G.; Czekaj, M.; Chu, V.; Spada, A.P.; Gong, Y.; Gao, J.; Colussi, D.J.; Amido-(propyl and allyl)-hydroxybenzamidines: Development of achiral inhibitors of factor Xa. Bioorg Med Chem Lett 2000, 10, 3, 217.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	46459	4-[4-(methoxycarbonyl)phenyl]-1-pyridiniumolate	C₁₃H₁₁NO₃	详情	详情
(II)	46460	methyl 4-(2-cyano-4-pyridinyl)benzoate	C₁₄H₁₀N₂O₂	详情	详情
(III)	46461	4-[2-(aminocarbonyl)-4-pyridinyl]benzoic acid	C₁₃H₁₀N₂O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

3-Bromo-4-hydroxybenzonitrile (IV) was protected as the methoxymethyl ether (V). Subsequent Heck reaction with N-allyl phthalimide (VI) produced adduct (VII). The phthaloyl group OF (VII) was then removed by hydrazinolysis to yield the primary amine (VIII), which was coupled with carboxylic acid (III) using TBTU to afford amide (IX). Pinner reaction of (IX) with concomitant methoxymethyl group deprotection gave imidate (X). Finally, ammonolysis of the imidate group of (X) furnished the title amidine.

参考文献中间体

合成目标

【1】 Pauls, H.W.; Brown, K.D.; Liang, G.; Czekaj, M.; Chu, V.; Spada, A.P.; Gong, Y.; Gao, J.; Colussi, D.J.; Amido-(propyl and allyl)-hydroxybenzamidines: Development of achiral inhibitors of factor Xa. Bioorg Med Chem Lett 2000, 10, 3, 217.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(III)	46461	4-[2-(aminocarbonyl)-4-pyridinyl]benzoic acid		C₁₃H₁₀N₂O₃	详情	详情
(IV)	46462	3-bromo-4-hydroxybenzonitrile	2315-86-8	C₇H₄BrNO	详情	详情
(V)	46463	3-bromo-4-(methoxymethoxy)benzonitrile		C₉H₈BrNO₂	详情	详情
(VI)	46464	2-allyl-1H-isoindole-1,3(2H)-dione		C₁₁H₉NO₂	详情	详情
(VII)	46465	3-[(E)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-propenyl]-4-(methoxymethoxy)benzonitrile		C₂₀H₁₆N₂O₄	详情	详情
(VIII)	46466	3-[(E)-3-amino-1-propenyl]-4-(methoxymethoxy)benzonitrile		C₁₂H₁₄N₂O₂	详情	详情
(IX)	46467	4-[4-[([(E)-3-[5-cyano-2-(methoxymethoxy)phenyl]-2-propenyl]amino)carbonyl]phenyl]-2-pyridinecarboxamide		C₂₅H₂₂N₄O₄	详情	详情
(X)	46468	ethyl 3-[(E)-3-([4-[2-(aminocarbonyl)-4-pyridinyl]benzoyl]amino)-1-propenyl]-4-hydroxybenzenecarboximidoate		C₂₅H₂₄N₄O₄	详情	详情

Extended Information