2-([[(4S)-4-([4-[2-(2,4-diamino-6-pteridinyl)ethyl]benzoyl]amino)-5-methoxy-5-oxopentyl]amino]carbonyl)benzoic acid -Drug Synthesis Database

【结构式】

【分子编号】42887

【品名】2-([[(4S)-4-([4-[2-(2,4-diamino-6-pteridinyl)ethyl]benzoyl]amino)-5-methoxy-5-oxopentyl]amino]carbonyl)benzoic acid

【CA登记号】

【分子式】C₂₉H₃₀N₈O₆

【分子量】586.60752

【元素组成】C 59.38% H 5.15% N 19.1% O 16.36%

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：(XV)

An alternative route involved a Wittig reaction between aldehyde (IV) and ylide (XI), generated from 2-amino-3-cyanopyrazin-5-ylmethyltriphenylphosphonium chloride (X). The resulting adduct (XII) was then cyclized and partly hydrolyzed to pteridine (XIV) upon refluxing with guanidine (XIII) in MeOH. Catalytic hydrogenation and further reoxidation of (XIV) yielded (XV). The methyl ester group of (XV) was finally hydrolyzed by treatment with NaOH in DMSO.

参考文献中间体

合成目标

【1】 Rosowsky, A.; Vaidya, C.M.; Wright, J.E.; Forsch, R.A.; Bader, H.; Analogues of the potent nonpolyglutamatable antifolate Nalpha-(4-amino-4-deoxypteroyl)-Ndelta-hemiphthaloyl-L-ornithine (PT523) with modifications in the side chain, p-aminobenzoyl moiety, or 9,10-bridge: Synthesis and in vitro antitumor activity. J Med Chem 2000, 43, 8, 1620.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIIa)	42883	methyl (2S)-2-([4-[(E)-2-(5-amino-6-cyano-2-pyrazinyl)ethenyl]benzoyl]amino)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanoate		C₂₈H₂₄N₆O₅	详情	详情
(XIVa)	42885	2-([[(4S)-4-([4-[(E)-2-(2,4-diamino-6-pteridinyl)ethenyl]benzoyl]amino)-5-methoxy-5-oxopentyl]amino]carbonyl)benzoic acid		C₂₉H₂₈N₈O₆	详情	详情
(XIVb)	42886	2-([[(4S)-4-([4-[(Z)-2-(2,4-diamino-6-pteridinyl)ethenyl]benzoyl]amino)-5-methoxy-5-oxopentyl]amino]carbonyl)benzoic acid		C₂₉H₂₈N₈O₆	详情	详情
(XIIb)	42887	2-([[(4S)-4-([4-[2-(2,4-diamino-6-pteridinyl)ethyl]benzoyl]amino)-5-methoxy-5-oxopentyl]amino]carbonyl)benzoic acid		C₂₉H₃₀N₈O₆	详情	详情
(IV)	42876	methyl (2S)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-[(4-formylbenzoyl)amino]pentanoate		C₂₂H₂₀N₂O₆	详情	详情
(X)	42881	[(5-amino-6-cyano-2-pyrazinyl)methyl](triphenyl)phosphonium chloride		C₂₄H₂₀ClN₄P	详情	详情
(XI)	42882	3-amino-6-[(triphenylphosphoranylidene)methyl]-2-pyrazinecarbonitrile		C₂₄H₁₉N₄P	详情	详情
(XIII)	14790	Guanidine	113-00-8	CH₅N₃	详情	详情
(XV)	42887	2-([[(4S)-4-([4-[2-(2,4-diamino-6-pteridinyl)ethyl]benzoyl]amino)-5-methoxy-5-oxopentyl]amino]carbonyl)benzoic acid		C₂₉H₃₀N₈O₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XIIb)

参考文献中间体

合成目标

【1】 Rosowsky, A.; Vaidya, C.M.; Wright, J.E.; Forsch, R.A.; Bader, H.; Analogues of the potent nonpolyglutamatable antifolate Nalpha-(4-amino-4-deoxypteroyl)-Ndelta-hemiphthaloyl-L-ornithine (PT523) with modifications in the side chain, p-aminobenzoyl moiety, or 9,10-bridge: Synthesis and in vitro antitumor activity. J Med Chem 2000, 43, 8, 1620.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIIa)	42883	methyl (2S)-2-([4-[(E)-2-(5-amino-6-cyano-2-pyrazinyl)ethenyl]benzoyl]amino)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanoate		C₂₈H₂₄N₆O₅	详情	详情
(XIVa)	42885	2-([[(4S)-4-([4-[(E)-2-(2,4-diamino-6-pteridinyl)ethenyl]benzoyl]amino)-5-methoxy-5-oxopentyl]amino]carbonyl)benzoic acid		C₂₉H₂₈N₈O₆	详情	详情
(XIVb)	42886	2-([[(4S)-4-([4-[(Z)-2-(2,4-diamino-6-pteridinyl)ethenyl]benzoyl]amino)-5-methoxy-5-oxopentyl]amino]carbonyl)benzoic acid		C₂₉H₂₈N₈O₆	详情	详情
(XIIb)	42887	2-([[(4S)-4-([4-[2-(2,4-diamino-6-pteridinyl)ethyl]benzoyl]amino)-5-methoxy-5-oxopentyl]amino]carbonyl)benzoic acid		C₂₉H₃₀N₈O₆	详情	详情
(IV)	42876	methyl (2S)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-[(4-formylbenzoyl)amino]pentanoate		C₂₂H₂₀N₂O₆	详情	详情
(X)	42881	[(5-amino-6-cyano-2-pyrazinyl)methyl](triphenyl)phosphonium chloride		C₂₄H₂₀ClN₄P	详情	详情
(XI)	42882	3-amino-6-[(triphenylphosphoranylidene)methyl]-2-pyrazinecarbonitrile		C₂₄H₁₉N₄P	详情	详情
(XIII)	14790	Guanidine	113-00-8	CH₅N₃	详情	详情
(XV)	42887	2-([[(4S)-4-([4-[2-(2,4-diamino-6-pteridinyl)ethyl]benzoyl]amino)-5-methoxy-5-oxopentyl]amino]carbonyl)benzoic acid		C₂₉H₃₀N₈O₆	详情	详情

Extended Information