1H,3H-furo[3,4-f][2]benzofuran-1,3,5,7-tetrone -Drug Synthesis Database

【结构式】

【分子编号】41484

【品名】1H,3H-furo[3,4-f][2]benzofuran-1,3,5,7-tetrone

【CA登记号】89-32-7

【分子式】C₁₀H₂O₆

【分子量】218.12228

【元素组成】C 55.07% H 0.92% O 44.01%

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：(VI)

Reaction of 4-methylphenol (I) with NaH in DMF and 3-fluorobenzaldehyde (II) yields aldehyde (III), which will be converted into secondary amine (V) via a reductive amination with amine (IV) in presence of NaBH3CN in MeOH and catalytic HOAc. Amine (V) couples with dianhydride (VI) in THF in presence of NMM or alternatively in toluene and Et3N. Final treatment with Na2CO3 in THF yields the desired product.

参考文献中间体

合成目标

【1】 Sullivan, G.M.; Rosenberg, S.H.; Prasad, R.N.; O'Connor, S.J.; Donner, B.G.; Fakhoury, S.A.; Fung, K.L.; Stout, D.M.; Rockway, T.W.; Baker, W.R.; Shen, W.; Garvey, D.S. (Abbott Laboratories Inc.); Benzene, pyridine, naphthalene or benzophenone derivs. as inhibitors of squalene synthetase and protein farnesyltransferase. WO 9634851 .

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)	37678	p-cresol	106-44-5	C₇H₈O	详情	详情
(II)	18887	3-Fluorobenzaldehyde	456-48-4	C₇H₅FO	详情	详情
(III)	41482	3-(4-methylphenoxy)benzaldehyde	79124-75-7	C₁₄H₁₂O₂	详情	详情
(IV)	38253	2-ethoxybenzylamine; (2-ethoxyphenyl)methanamine		C₉H₁₃NO	详情	详情
(V)	41483	N-(2-ethoxybenzyl)[3-(4-methylphenoxy)phenyl]methanamine; N-(2-ethoxybenzyl)-N-[3-(4-methylphenoxy)benzyl]amine	n/a	C₂₃H₂₅NO₂	详情	详情
(VI)	41484	1H,3H-furo[3,4-f][2]benzofuran-1,3,5,7-tetrone	89-32-7	C₁₀H₂O₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The reductive alkylation of (S)-1,2,3,4-tetrahydro-1-naphthalenylamine (I) with 3-phenoxybenzaldehyde (II) in the presence of NaBH4 affords the secondary amine (III), which is then acylated with 1,2,4,5-benzenetetracarboxylic dianhydride (IV), followed by aqueous hydrolysis to furnish the title compound.

参考文献中间体

合成目标

【1】 Lee, C.-H.; Stewart, A.O.; Perner, R.J.; Zheng, G.Z.; Larson, D.P.; Koenig, J.R.; Gomtsyan, A.R.; Didomenico, S.; Bayburt, E.K. (Abbott Laboratories Inc.); Trisubstd.-N-[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]benzamides which inhibit P2X3 and P2X2/3 containing receptors. US 2002173665; WO 0294767 .

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)	63324	(1S)-1,2,3,4-tetrahydro-1-naphthalenamine; (1S)-1,2,3,4-tetrahydro-1-naphthalenylamine		C₁₀H₁₃N	详情	详情
(II)	63325	3-phenoxybenzaldehyde		C₁₃H₁₀O₂	详情	详情
(III)	63326	(1S)-N-(3-phenoxybenzyl)-1,2,3,4-tetrahydro-1-naphthalenamine; N-(3-phenoxybenzyl)-N-[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amine		C₂₃H₂₃NO	详情	详情
(IV)	41484	1H,3H-furo[3,4-f][2]benzofuran-1,3,5,7-tetrone	89-32-7	C₁₀H₂O₆	详情	详情

Extended Information