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【结 构 式】

【分子编号】50080

【品名】N-(7-chloro-6-nitro-4-quinazolinyl)-N-(4-chlorophenethyl)amine; 7-chloro-N-(4-chlorophenethyl)-6-nitro-4-quinazolinamine

【CA登记号】

【 分 子 式 】C16H12Cl2N4O2

【 分 子 量 】363.20244

【元素组成】C 52.91% H 3.33% Cl 19.52% N 15.43% O 8.81%

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:(V)

Nitration of quinazolone (I) by reaction with HNO3/H2SO4 affords 7-chloro-6-nitro-4-quinazolone (II), which is then chlorinated with phosphorus oxychloride (POCl3) to provide quinazoline (III). Selective amination of the quinazoline ring of (III) by reaction with 4-chlorophenethylamine (IV) in isopropanol in the presence of Et3N yields compound (V), which is finally converted into the desired compound by condensation with piperazine (VI) in refluxing butanol in the presence of DIEA. Alternatively the target product can be obtained by the following procedure: Condensation of quinazolone derivative (II) with piperazine (VI) in refluxing butanol in the presence of DIEA affords compound (VII), which is treated with POCl3 and finally subjected to condensation with 4-chlorophenethylamine (IV) in isopropanol in the presence of Et3N.

1 Matsumoto, M.; Hayashi, H.; Tomizawa, H.; Obara, F.; Nagasaki, T.; Tobe, M.; Isoba, Y.; Structure-activity relationships of quinazoline derivatives: Dual-acting compounds with inhibitory activities toward both TNF-alpha production and T cell proliferation. Bioorg Med Chem Lett 2001, 11, 4, 545.
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) 50077 7-chloro-4(3H)-quinazolinone C8H5ClN2O 详情 详情
(II) 50078 7-chloro-6-nitro-4(3H)-quinazolinone C8H4ClN3O3 详情 详情
(III) 50079 4,7-dichloro-6-nitroquinazoline C8H3Cl2N3O2 详情 详情
(IV) 38459 methyl (2R,3R)-3-amino-2-(3-cyanobenzyl)butanoate C13H16N2O2 详情 详情
(V) 50080 N-(7-chloro-6-nitro-4-quinazolinyl)-N-(4-chlorophenethyl)amine; 7-chloro-N-(4-chlorophenethyl)-6-nitro-4-quinazolinamine C16H12Cl2N4O2 详情 详情
(VI) 10355 Diethylenediamine; Piperazine 110-85-0 C4H10N2 详情 详情
(VII) 50081 6-nitro-7-(1-piperazinyl)-4(3H)-quinazolinone C12H13N5O3 详情 详情
Extended Information