【结 构 式】 |
【分子编号】25232 【品名】5-acetyl-2-propyl-3-[[2'-(1-trityl-1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-4-carboxylic acid 【CA登记号】 |
【 分 子 式 】C45H41N7O3 【 分 子 量 】727.86592 【元素组成】C 74.26% H 5.68% N 13.47% O 6.59% |
合成路线1
该中间体在本合成路线中的序号:(III)Hemifumarate salt (I) was liberated by treatment with NaHCO3 and subsequently protected with trityl chloride to afford (II). Then, the methyl ester function of (II) was hydrolyzed with NaOH to furnish acid (III). Chlorination of methyl chloroformate (IV) with sulfuryl chloride in the presence of a catalytic amount of azobis(isobutyronitrile) (AIBN) yielded chloromethyl chloroformate (V), which was condensed with 3-pentanol (VI) in pyridine to provide carbonate (VII). The O-alkylation of acid (III) with 3-pentyloxycarbonyloxymethyl chloride (VII) in the presence of K2CO3 in DMF produced the pentyloxycarbonyloxymethyl ester (VIII). Finally, the trityl protecting group of (VIII) was removed with 85% formic acid at r.t., and the resulting product was converted to the hydrochloride salt by treatment with an ethanolic solution of HCl.
【1】 Sekine, Y.; Kawanishi, E.; Narita, H.; Hashimoto, Y.; Mizobe, M. (Tanabe Seiyaku Co., Ltd.); Imidazopyridine derivs. and process for preparing the same. CA 2146802; EP 0682023; JP 1996003162; US 5753672 . |
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) | 25230 | methyl 5-acetyl-2-propyl-3-[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-4-carboxylate | C27H29N7O3 | 详情 | 详情 | |
(II) | 25231 | methyl 5-acetyl-2-propyl-3-[[2'-(1-trityl-1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-4-carboxylate | C46H43N7O3 | 详情 | 详情 | |
(III) | 25232 | 5-acetyl-2-propyl-3-[[2'-(1-trityl-1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-4-carboxylic acid | C45H41N7O3 | 详情 | 详情 | |
(IV) | 16993 | methyl chlorocarbonate;Carbonochloridic acid methyl ester;[(chlorocarbonyl)oxy]methane;methyl chloroformate | 79-22-1 | C2H3ClO2 | 详情 | 详情 |
(V) | 19249 | Chloromethyl chloroformate; Chloro[(chlorocarbonyl)oxy]methane | 22128-62-7 | C2H2Cl2O2 | 详情 | 详情 |
(VI) | 21970 | 3-pentanol | 584-02-1 | C5H12O | 详情 | 详情 |
(VII) | 25234 | chloromethyl 1-ethylpropyl carbonate | C7H13ClO3 | 详情 | 详情 | |
(VIII) | 25233 | [[(1-ethylpropoxy)carbonyl]oxy]methyl 5-acetyl-2-propyl-3-[[2'-(1-trityl-1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-4-carboxylate | C52H53N7O6 | 详情 | 详情 |