7-chloro-6-nitro-2,4(1H,3H)-quinazolinedione -Drug Synthesis Database

【结构式】

【分子编号】54831

【品名】7-chloro-6-nitro-2,4(1H,3H)-quinazolinedione

【CA登记号】

【分子式】C₈H₄ClN₃O₄

【分子量】241.59028

【元素组成】C 39.77% H 1.67% Cl 14.67% N 17.39% O 26.49%

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：(XIII)

In an improved procedure, commercial 7-chloroquinazolinedione (XII) was nitrated to (XIII) using 60% HNO3 in the presence of H2SO4. Subsequent chloro displacement in (XIII) with ethylamine in hot DMSO furnished nitro amine (XIV). Chlorination of quinazolinedione (XIV) to the dichloro derivative (XV) was carried out by means of POCl3 in the presence of diisopropylethylamine in hot toluene. The 4-chloro group of (XV) was regioselectively displaced by the intermediate benzylamine (IV) yielding (XVI). Simultaneous reduction of the nitro and chloro groups of (XVI) by transfer hydrogenation provided the phenylenediamine (XI). The imidazothione ring was finally constructed by condensation of (XI) with phenyl isothiocyanate.

参考文献中间体

合成目标

【1】 Fujino, K.; et al.; Development of a practical synthetic route of a PDE V inhibitor KF31327. Org Process Res Dev 2001, 5, 4, 426.
【2】 Fujino, K.; et al.; Process development of a PDE V inhibitor KF31327. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst ORGN 612.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IV)	54825	{1-[2-(aminomethyl)phenyl]-4-piperidinyl}methanol	C₁₃H₂₀N₂O	详情	详情
(XI)	54829	{1-[2-({[6-amino-7-(ethylamino)-4-quinazolinyl]amino}methyl)phenyl]-4-piperidinyl}methanol	C₂₃H₃₀N₆O	详情	详情
(XII)	54830	7-chloro-2,4(1H,3H)-quinazolinedione	C₈H₅ClN₂O₂	详情	详情
(XIII)	54831	7-chloro-6-nitro-2,4(1H,3H)-quinazolinedione	C₈H₄ClN₃O₄	详情	详情
(XIV)	54832	7-(ethylamino)-6-nitro-2,4(1H,3H)-quinazolinedione	C₁₀H₁₀N₄O₄	详情	详情
(XV)	54833	N-(2,4-dichloro-6-nitro-7-quinazolinyl)-N-ethylamine; 2,4-dichloro-N-ethyl-6-nitro-7-quinazolinamine	C₁₀H₈Cl₂N₄O₂	详情	详情
(XVI)	54834	{1-[2-({[2-chloro-7-(ethylamino)-6-nitro-4-quinazolinyl]amino}methyl)phenyl]-4-piperidinyl}methanol	C₂₃H₂₇ClN₆O₃	详情	详情

Extended Information