4,7-dichloro-6-nitroquinazoline -Drug Synthesis Database

【结构式】

【分子编号】50079

【品名】4,7-dichloro-6-nitroquinazoline

【CA登记号】

【分子式】C₈H₃Cl₂N₃O₂

【分子量】244.03624

【元素组成】C 39.37% H 1.24% Cl 29.06% N 17.22% O 13.11%

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：(III)

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.

参考文献中间体

合成目标

【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