2-[4-(2-quinolinylmethoxy)phenyl]-1-ethanol -Drug Synthesis Database

【结构式】

【分子编号】47356

【品名】2-[4-(2-quinolinylmethoxy)phenyl]-1-ethanol

【CA登记号】

【分子式】C₁₈H₁₇NO₂

【分子量】279.33852

【元素组成】C 77.4% H 6.13% N 5.01% O 11.46%

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：(III)

Condensation of 4-hydroxyphenylethanol (I) with 2-(chloromethyl)quinoline (II) in ethanolic KOH provided ether (III). The free hydroxyl group of (III) was then converted to the corresponding mesylate (IV) by treatment with methanesulfonyl chloride and Et3N. Alkylation of 11-(4-piperidinylidene)-6,11-dihydro-5H-imidazo[2,1-b][3]benzazepine-3-methanol (V) with mesylate (IV) in the presence of NaHCO3 gave adduct (VI). The primary alcohol of (VI) was oxidized to aldehyde (VII) using MnO2 in CH2Cl2. Finally, aldehyde (VII) was further oxidized to the title methyl ester by means of MnO2 in the presence of sodium cyanate in HOAc-MeOH.

参考文献中间体

合成目标

【1】 Janssens, F.E.; Leenaerts, J.E.; Sommen, F.M.; Surleraux, D.L.N.G. (Janssen Pharmaceutica NV); Fused imidazole derivs. as multidrug resistance modulators. EP 0888352; JP 2000505477; US 6218381; WO 9734897 .
【2】 Snoeck, H.J.M. (Janssen Pharmaceutica NV); Fused imidazole derivs. for improving oral bioavailability of pharmaceutical agents. WO 9913871 .

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)	47355	4-(2-hydroxyethyl)phenol	501-94-0	C₈H₁₀O₂	详情	详情
(II)	13162	2-(Chloromethyl)quinoline; alpha-Chloroquinaldine	4377-41-7	C₁₀H₈ClN	详情	详情
(III)	47356	2-[4-(2-quinolinylmethoxy)phenyl]-1-ethanol		C₁₈H₁₇NO₂	详情	详情
(IV)	47357	4-(2-quinolinylmethoxy)phenethyl methanesulfonate		C₁₉H₁₉NO₄S	详情	详情
(V)	47358	[11-(4-piperidinylidene)-6,11-dihydro-5H-imidazo[2,1-b][3]benzazepin-3-yl]methanol		C₁₈H₂₁N₃O	详情	详情
(VI)	47359	(11-[1-[4-(2-quinolinylmethoxy)phenethyl]-4-piperidinylidene]-6,11-dihydro-5H-imidazo[2,1-b][3]benzazepin-3-yl)methanol		C₃₆H₃₆N₄O₂	详情	详情
(VII)	47360	11-[1-[4-(2-quinolinylmethoxy)phenethyl]-4-piperidinylidene]-6,11-dihydro-5H-imidazo[2,1-b][3]benzazepine-3-carbaldehyde		C₃₆H₃₄N₄O₂	详情	详情

Extended Information