1-[2-(4-benzylphenoxy)ethyl]-1H-imidazo[4,5-c]pyridin-5-ium-5-olate -Drug Synthesis Database

【结构式】

【分子编号】64441

【品名】1-[2-(4-benzylphenoxy)ethyl]-1H-imidazo[4,5-c]pyridin-5-ium-5-olate

【CA登记号】

【分子式】C₂₁H₁₉N₃O₂

【分子量】345.40088

【元素组成】C 73.03% H 5.54% N 12.17% O 9.26%

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：(X)

Alkylation of 4-hydroxydiphenylmethane (I) with tert-butyl bromoacetate (II) in the presence of NaH and Bu4NI in DMF affords ether (III). The ester function of (III) is then reduced by LiAlH4 to furnish the primary alcohol (IV), which is subsequently activated as the corresponding tosylate (V) (1,2). Condensation of tosylate (V) with 5-azabenzimidazole (VI) gives rise to a mixture of the three possible regioisomers (VII), (VIII) and (IX), which can be separated by means of flash chromatography. The desired isomer (IX) is then converted to the N-oxide (X) employing m-chloroperbenzoic acid in CHCl3 (1-3). Finally, reaction of N-oxide (X) with cyanotrimethylsilane produces the target nitrile (3).

参考文献中间体

合成目标

【1】 Synthesis of imidazopyridines and purines as potent inhibitors of leukotriene A4 hydrolase. Bioorg Med Chem Lett 2003, 13, 6, 1137.
【2】 Chandrakumar, N.S.; Chen, B.B.; Clare, M.; Desai, B.N.; Djuric, S.W.; Docter, S.H.; Gasiecki, A.; Haack, R.A.; Liang, C.-D.; Miyashiro, J.M.; Penning, T.D.; Russell, M.A.; Yu, S.S. (Pfizer Inc.); LTA4 hydrolase inhibitors. EP 0804427; EP 1221441; JP 1998512848; WO 9611192 .
【3】 Chandrakumar, N.S.; Chen, B.B.; Clare, M.; Desai, B.N.; Djuric, S.W.; Docter, S.H.; Gasiecki, A.F.; Haack, R.A.; Liang, C.-D.; Miyashiro, J.M.; Penning, T.D.; Russell, M.A.; Yu, S.S. (Pfizer Inc.); LTA4 hydrolase inhibitor pharmaceutical compsns. and methods of use. JP 1998512542; WO 9610999 .

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)	50817	4-Hydroxydiphenylmethane; 4-Benzylphenol; alpha-Phenyl-p-cresol; p-Benzylphenol	101-53-1	C₁₃H₁₂O	详情	详情
(II)	17430	2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate	5292-43-3	C₆H₁₁BrO₂	详情	详情
(III)	64434	tert-butyl 2-(4-benzylphenoxy)acetate		C₁₉H₂₂O₃	详情	详情
(IV)	64435	2-(4-benzylphenoxy)-1-ethanol		C₁₅H₁₆O₂	详情	详情
(V)	64436	2-(4-benzylphenoxy)ethyl 4-methylbenzenesulfonate		C₂₂H₂₂O₄S	详情	详情
(VI)	64437	1H-imidazo[4,5-c]pyridine		C₆H₅N₃	详情	详情
(VII)	64438	4-benzylphenyl 2-(5H-imidazo[4,5-c]pyridin-5-yl)ethyl ether; 5-[2-(4-benzylphenoxy)ethyl]-5H-imidazo[4,5-c]pyridine		C₂₁H₁₉N₃O	详情	详情
(VIII)	64439	4-benzylphenyl 2-(3H-imidazo[4,5-c]pyridin-3-yl)ethyl ether; 3-[2-(4-benzylphenoxy)ethyl]-3H-imidazo[4,5-c]pyridine		C₂₁H₁₉N₃O	详情	详情
(IX)	64440	1-[2-(4-benzylphenoxy)ethyl]-1H-imidazo[4,5-c]pyridine; 4-benzylphenyl 2-(1H-imidazo[4,5-c]pyridin-1-yl)ethyl ether		C₂₁H₁₉N₃O	详情	详情
(X)	64441	1-[2-(4-benzylphenoxy)ethyl]-1H-imidazo[4,5-c]pyridin-5-ium-5-olate		C₂₁H₁₉N₃O₂	详情	详情

Extended Information