4-[(5-bromopentyl)oxy]-1,1'-biphenyl; [1,1'-biphenyl]-4-yl 5-bromopentyl ether -Drug Synthesis Database

【结构式】

【分子编号】53585

【品名】4-[(5-bromopentyl)oxy]-1,1'-biphenyl; [1,1'-biphenyl]-4-yl 5-bromopentyl ether

【CA登记号】n/a

【分子式】C₁₇H₁₉BrO

【分子量】319.24126

【元素组成】C 63.96% H 6% Br 25.03% O 5.01%

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：(II)

The known tricyclic bromide (I) was converted to the nitrile (II) by treatment with CuCN and NaCN. Addition of the Grignard reagent (IV), prepared from 4-chloro-1-methylpiperidine (III), to the tricyclic ketone (II) furnished the tertiary alcohol (V). This was finally dehydrated to the target piperidylidene derivative upon heating in the presence of SOCl2.

参考文献中间体

合成目标

【1】 Honda, H.; Mizuno, H.; Mogi, K.; Ito, Y.; Kaneko, Y.; Taido, N.; Sato, S.; Kuraishi, T. (SSP Co., Ltd.); Novel benzo[5,6]cyclohepta[1,2-b]pyridine derivs. and antiallergic agents comprising same. EP 0495484; JP 1993059040; US 5231101 .

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)	53284	8-bromo-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one	n/a	C₁₄H₁₀BrNO	详情	详情
(II)	53585	4-[(5-bromopentyl)oxy]-1,1'-biphenyl; [1,1'-biphenyl]-4-yl 5-bromopentyl ether	n/a	C₁₇H₁₉BrO	详情	详情
(III)	20949	4-Chloro-1-methylpiperidine; 4-Chloro-N-methylpiperidine; N-methyl-4-chloropiperidine	55770-77-4	C₆H₁₂ClN	详情	详情
(IV)	20645	chloro(1-methyl-4-piperidinyl)magnesium		C₆H₁₂ClMgN	详情	详情
(V)	53286	11-hydroxy-11-(1-methyl-4-piperidinyl)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine-8-carbonitrile	n/a	C₂₁H₂₃N₃O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

The reaction of pyridine-4-amine (I) with 2-chloroethyl isocyanate (II) in toluene gives N-(2-chloroethyl)-N'-(4-pyridyl)urea (III), which is cyclized by means of NaH in DMF/THF, yielding 1-(4-pyridyl)imidazolidin-2-one (IV). Finally, this compound is condensed with 4-(5-bromopentyloxy)biphenyl (V) by means of NaH in DMF to afford the target disubstituted imidazolidinone. (1,2)

参考文献中间体

合成目标

【1】 Chang, C.-M.; Li, W.-T.; Shia, K.-S.; et al.; Design, synthesis, and structure-activity relationship of pyridyl imidazolidinones: A novel class of potent and selective human enterovirus 71 inhibitors. J Med Chem 2002, 45, 8, 1644.
【2】 Hsu, M.-C.; Li, W.-T.; Chang, C.-M.; Shia, K.-S.; Shih, S.-R.; Chern, J.-H.; Chen, S.-J. (National Health Research Institutes); Imidazolidinone cpds.. US 2003087936; US 6706739 .

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)	25661	4-pyridinamine; 4-aminopyridine	5044-74-5	C₅H₆N₂	详情	详情
(II)	11237	1-Chloro-2-isocyanatoethane; 2-Chloroethyl isocyanate	1943-83-5	C₃H₄ClNO	详情	详情
(III)	53583	N-(2-chloroethyl)-N'-(4-pyridinyl)urea	62491-96-7	C₈H₁₀ClN₃O	详情	详情
(IV)	53584	1-(4-pyridinyl)-2-imidazolidinone	n/a	C₈H₉N₃O	详情	详情
(V)	53585	4-[(5-bromopentyl)oxy]-1,1'-biphenyl; [1,1'-biphenyl]-4-yl 5-bromopentyl ether	n/a	C₁₇H₁₉BrO	详情	详情

Extended Information