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【结 构 式】

【分子编号】27756

【品名】1-(3-cyclopentylpropyl)-4-phenyl-1,4-dihydro-5H-1,2,3,4-tetraazol-5-one

【CA登记号】

【 分 子 式 】C15H20N4O

【 分 子 量 】272.35016

【元素组成】C 66.15% H 7.4% N 20.57% O 5.87%

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:(XX)

Cyclopentylpropanol (XV) was converted to mesylate (XVI) and subsequently treated with NaI to give iodide (XVII). Then, alkylation of phenyltetrazolone (XIX), (obtained from phenyl isocyanate (XVIII) and aluminum azide), with iodide (XVII) afforded the substituted tetrazolone (XX). Nitration of the phenyl ring of (XX) employing nitronium tetrafluoborate produced the 4-nitro derivative (XXI) along with minor amounts of the 2-nitro isomer, which was separated by flash chromatography. After catalytic hydrogenation of the nitro group of (XXI) to aniline (XXII), diazotization, followed by treatment with an AcOH solution of SO2 in the presence of CuCl furnished sulfonyl chloride (XXIII). Coupling of this sulfonyl chloride with the intermediate amine (VII) in the presence of pyridine gave sulfonamide (XXIV). Finally, the Boc protecting group of (XXIV) was removed by acidic treatment to provide the title compound.

1 Shih, T.L.; Candelore, M.R.; Cascieri, M.A.; L-770,644: A potent and selective human beta3 adrenergic receptor agonist with improved oral bioavailability. Bioorg Med Chem Lett 1999, 9, 9, 1251.
2 Fisher, M.H.; Naylor, E.M.; Ok, D.; Weber, A.E.; Shih, T.; Ok, H. (Merck & Co., Inc.); Substd. sulfonamides as selective beta3 agonists for the treatment of diabetes and obesity. EP 0757674; JP 1997512275; US 5541197; US 5561142; WO 9529159 .
3 Smith, R.G. (Merck & Co., Inc.); Combination therapy for the treatment of diabetes and obesity. JP 1999515027; WO 9716189 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 26553 tert-butyl 4-aminophenethyl[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]carbamate C20H27N3O3 详情 详情
(XV) 27752 3-cyclopentyl-1-propanol 767-05-5 C8H16O 详情 详情
(XVI) 27753 3-cyclopentylpropyl methanesulfonate C9H18O3S 详情 详情
(XVII) 27754 1-(3-iodopropyl)cyclopentane C8H15I 详情 详情
(XVIII) 11289 1-Isocyanatobenzene; phenyl isocyanate; Phenylisocyanate 103-71-9 C7H5NO 详情 详情
(XIX) 27755 1-phenyl-1,4-dihydro-5H-1,2,3,4-tetraazol-5-one C7H6N4O 详情 详情
(XX) 27756 1-(3-cyclopentylpropyl)-4-phenyl-1,4-dihydro-5H-1,2,3,4-tetraazol-5-one C15H20N4O 详情 详情
(XXI) 27757 1-(3-cyclopentylpropyl)-4-(4-nitrophenyl)-1,4-dihydro-5H-1,2,3,4-tetraazol-5-one C15H19N5O3 详情 详情
(XXII) 27758 1-(4-aminophenyl)-4-(3-cyclopentylpropyl)-1,4-dihydro-5H-1,2,3,4-tetraazol-5-one C15H21N5O 详情 详情
(XXIII) 27759 4-[4-(3-cyclopentylpropyl)-5-oxo-4,5-dihydro-1H-1,2,3,4-tetraazol-1-yl]benzenesulfonyl chloride C15H19ClN4O3S 详情 详情
(XXIV) 27760 tert-butyl 4-[([4-[4-(3-cyclopentylpropyl)-5-oxo-4,5-dihydro-1H-1,2,3,4-tetraazol-1-yl]phenyl]sulfonyl)amino]phenethyl[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]carbamate C35H45N7O6S 详情 详情
Extended Information