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【结 构 式】

【药物名称】SX-5216, AC-5216

【化学名称】N-Benzyl-N-ethyl-2-(7-methyl-8-oxo-2-phenyl-7,8-dihydro-9H-purin-9-yl)acetamide

【CA登记号】226954-04-7

【 分 子 式 】C23H23N5O2

【 分 子 量 】401.47206

【开发单位】Dainippon Pharmaceutical (Originator), Novartis (Licensee)

【药理作用】Antidepressants, Anxiolytics, Mood Disorders, Treatment of, PSYCHOPHARMACOLOGIC DRUGS, GABA(A) BZ Site Receptor Agonists

合成路线1

Pyrimidinone (III) was formed by condensation of benzamidine hydrochloride (I) with diethyl (ethoxymethylene)malonate (II). Subsequent reaction with glycinamide derivative (V) in the presence of p-tosyl chloride and Et3N afforded the aminopyrimidine (VI) (1). Alternatively, aminopyrimidine (VI) was prepared by chlorination of pyrimidinone (III) with POCl3, followed by displacement of the resulting chloropyrimidine (IV) with glycinamide (V) (2). Basic hydrolysis of the ethyl ester group of (VI) furnished pyrimidinecarboxylic acid (VII). This was then subjected to a Curtius rearrangement employing diphenyl phosphoryl azide (DPPA) to produce the 8-oxopurine system (VIII). Finally, N-alkylation of (VIII) with iodomethane gave rise to the title compound.

1 Masumoto, K.; et al.; SX-5216, highly potent and selective mitochondrial benzodiazepine receptor ligand as a potential anxiolytic agent. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 113.
2 Matsumoto, K.; Kondo, K.; Furukawa, K.; Murata, T.; Oka, M. (Dainippon Pharmaceutical Co., Ltd.); 2-Aryl-8-oxodihydropurine derivs., process for producing the same, medicinal compsns. containing the same, and intermediates thereof. EP 1036794; WO 9928320 .
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) 37052 Benzamidine; benzenecarboximidamide C7H8N2 详情 详情
(II) 14088 Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate 87-13-8 C10H16O5 详情 详情
(III) 40809 ethyl 6-oxo-2-phenyl-1,6-dihydro-5-pyrimidinecarboxylate C13H12N2O3 详情 详情
(IV) 40810 ethyl 4-chloro-2-phenyl-5-pyrimidinecarboxylate C13H11ClN2O2 详情 详情
(V) 40811 2-amino-N-benzyl-N-ethylacetamide C11H16N2O 详情 详情
(VI) 40812 ethyl 4-([2-[benzyl(ethyl)amino]-2-oxoethyl]amino)-2-phenyl-5-pyrimidinecarboxylate C24H26N4O3 详情 详情
(VII) 40813 4-([2-[benzyl(ethyl)amino]-2-oxoethyl]amino)-2-phenyl-5-pyrimidinecarboxylic acid C22H22N4O3 详情 详情
(VIII) 40814 N-benzyl-N-ethyl-2-(8-oxo-2-phenyl-7,8-dihydro-9H-purin-9-yl)acetamide C22H21N5O2 详情 详情
Extended Information