N-[2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-1H-indole-5-carboxamide -Drug Synthesis Database

【结构式】

【分子编号】48619

【品名】N-[2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-1H-indole-5-carboxamide

【CA登记号】

【分子式】C₂₀H₂₂N₂O₅

【分子量】370.40516

【元素组成】C 64.85% H 5.99% N 7.56% O 21.6%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(V)

Condensation of 3,4,5-trimethoxybenzaldehyde (I) with nitromethane in the presence of KOH produced the nitro alcohol (II), which was subsequently hydrogenated over Pd/C to afford amino alcohol (III). Acylation of (III) with 5-indolecarboxylic acid (IV) gave the corresponding amide (V). Oxazoline (VI) was then obtained by cyclization of (V) in the presence of Burgess reagent. Finally, N-methylation of the indole ring with MeI and KOH furnished the title compound.

参考文献中间体

合成目标

【1】 Liu, G.; Jae, H.-S.; Szczepankiewicz, B.G.; et al.; New antimitotic agents with activity in multi-drug-resistant cell lines and in vivo efficacy in murine tumor models. J Med Chem 2001, 44, 25, 4416.
【2】 Woods, K.W.; Wang, L.; Kalvin, D.M.; Barr, K.J.; Li, Q.; Liu, G.; Gwaltney, S.L. II; Claiborne, A.K.; Jae, H.-S.; Sham, H.L. (Abbott Laboratories Inc.); Substd. oxazolines as antiproliferative agents. WO 0006556 .
【3】 Sham, H.L.; Jae, H.-S.; Li, Q.; Wang, L.; Woods, K.W.; Liu, G.; Barr, K.J.; Kalvin, D.M.; Gwaltney, S.L. II; Claiborne, A.K. (Abbott Laboratories Inc.); Oxazoline antiproliferative agents. US 6228868 .

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)	11136	3,4,5-Trimethoxybenzaldehyde	86-81-7	C₁₀H₁₂O₄	详情	详情
(II)	48616	2-nitro-1-(3,4,5-trimethoxyphenyl)-1-ethanol		C₁₁H₁₅NO₆	详情	详情
(III)	48617	2-amino-1-(3,4,5-trimethoxyphenyl)-1-ethanol		C₁₁H₁₇NO₄	详情	详情
(IV)	48618	Indole-5-carboxylic acid	1670-81-1	C₉H₇NO₂	详情	详情
(V)	48619	N-[2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-1H-indole-5-carboxamide		C₂₀H₂₂N₂O₅	详情	详情
(VI)	48620	5-[5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1,3-oxazol-2-yl]-1H-indole; 4-[2-(1H-indol-5-yl)-4,5-dihydro-1,3-oxazol-5-yl]-2,6-dimethoxyphenyl methyl ether		C₂₀H₂₀N₂O₄	详情	详情

Extended Information