2-[3-(3,4-dichlorophenyl)-1-[2-(3-isopropoxyphenyl)acetyl]-3-piperidinyl]ethyl methanesulfonate -Drug Synthesis Database

【结构式】

【分子编号】51325

【品名】2-[3-(3,4-dichlorophenyl)-1-[2-(3-isopropoxyphenyl)acetyl]-3-piperidinyl]ethyl methanesulfonate

【CA登记号】

【分子式】C₂₅H₃₁Cl₂NO₅S

【分子量】528.49628

【元素组成】C 56.82% H 5.91% Cl 13.42% N 2.65% O 15.14% S 6.07%

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：(II)

The known piperidinoethanol derivative (I) was converted to the mesylate (II) upon treatment with methanesulfonyl chloride and triethylamine. Displacement of the mesylate group of (II) with the spiro-substituted piperidine (III) provided adduct (IV). Finally, quaternization of piperidine (IV) with iodomethane gave the corresponding ammonium salt as a mixture of cis/trans isomers that were separated by column chromatography.

参考文献中间体

合成目标

【1】 Kubota, H.; Okamoto, Y.; Fujii, M.; Ikeda, K.; Takeuchi, M.; Shibanuma, T.; Isomura, Y.; Synthesis and NK1 receptor antagonistic activity of (±)-1-acyl-3-(3,4-dichlorophenyl)-3-[2-(spiro-substituted piperidin-1'-yl)ethyl]piperidines. Bioorg Med Chem Lett 1998, 8, 12, 1541.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	51324	1-[3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)-1-piperidinyl]-2-(3-isopropoxyphenyl)-1-ethanone	C₂₄H₂₉Cl₂NO₃	详情	详情
(II)	51325	2-[3-(3,4-dichlorophenyl)-1-[2-(3-isopropoxyphenyl)acetyl]-3-piperidinyl]ethyl methanesulfonate	C₂₅H₃₁Cl₂NO₅S	详情	详情
(III)	25126	1,2,3,4-tetrahydrospiro[isoquinoline-1,4'-piperidin]-3-one	C₁₃H₁₆N₂O	详情	详情
(IV)	51326		C₃₇H₄₃Cl₂N₃O₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The reaction of furan (I) with BuLi and Bu3Sn-Cl gives the bis tributyltin derivative (II), which is condensed with 4-bromobenzonitrile (III) by means of Pd(PPh3)4 in dioxane to yield 4,4'-(furan-2,5-diyl)-bis(benzonitrile) (IV). The reaction of (IV) with HCl and ethanol affords 4,4'-(furan-2,5-diyl)bis(ethyl benzimidate) (V), which is finally treated with O-methylhydroxylamine in ethanol to provide the target bis-O-methyl benzamidoxime.

参考文献中间体

合成目标

【1】 McChesney-Harris, L.; et al.; Synthesis, characterization, and formulation of DB289, a novel dication prodrug for the treatment of African sleeping sickness and Pneumocystis carinii pneumonia (PCP). 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-2162.

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)	22372	Furan	110-00-9	C₄H₄O	详情	详情
(II)	51325	2-[3-(3,4-dichlorophenyl)-1-[2-(3-isopropoxyphenyl)acetyl]-3-piperidinyl]ethyl methanesulfonate		C₂₅H₃₁Cl₂NO₅S	详情	详情
(III)	45833	4-Bromobenzonitrile	623-00-7	C₇H₄BrN	详情	详情
(IV)	35814	4-[5-(4-cyanophenyl)-2-furyl]benzonitrile		C₁₈H₁₀N₂O	详情	详情
(V)	35815	ethyl 4-(5-[4-[ethoxy(imino)methyl]phenyl]-2-furyl)benzenecarboximidoate		C₂₂H₂₂N₂O₃	详情	详情

Extended Information