6-nitro-4(3H)-quinazolinone -Drug Synthesis Database

【结构式】

【分子编号】34444

【品名】6-nitro-4(3H)-quinazolinone

【CA登记号】

【分子式】C₈H₅N₃O₃

【分子量】191.14612

【元素组成】C 50.27% H 2.64% N 21.98% O 25.11%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(III)

Condensation of 5-nitroanthranilic acid (I) with formamidine hydrochloride (II) at 210 C generated the quinazolinone (III). Subsequent alkylation of (III) at the 3-N atom with ethyl 4-bromobutyrate (IV) in the presence of K2CO3 in DMF produced the quinazoline-3-butyrate ester (V). Finally, catalytic hydrogenation of the nitro group of (V) using Pd/C yielded the corresponding 6-aminoquinazoline.

参考文献中间体

合成目标

【1】 Shih, H.; Deng, L.; Genini, D.; Cottam, H.B.; Leoni, L.M.; Chao, Q.; Carson, D.A.; Substituted isoquinolines and quinazolines as potential antiinflammatory agents. Synthesis and biological of inhibitors of tumor necrosis factor alpha. J Med Chem 1999, 42, 19, 3860.

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)	34443	2-amino-5-nitrobenzoic acid	616-79-5	C₇H₆N₂O₄	详情	详情
(II)	15369	Iminoformamide; Methanimidamide	463-52-5	CH₄N₂	详情	详情
(III)	34444	6-nitro-4(3H)-quinazolinone		C₈H₅N₃O₃	详情	详情
(IV)	11263	ethyl 4-bromobutanoate; Ethyl 4-bromobutyrate	2969-81-5	C₆H₁₁BrO₂	详情	详情
(V)	34445	ethyl 4-[6-nitro-4-oxo-3(4H)-quinazolinyl]butanoate		C₁₄H₁₅N₃O₅	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Chlorination of 6-nitro-4-quinazolone (I) in refluxing SOCl2 affords 4-chloro-6-nitroquinazoline (II), which is then condensed with 4-phenoxyphenethylamine (III) to furnish the 4-aminoquinazoline (IV). Finally, nitro group reduction employing iron powder and acetic acid gives rise to the title compound.

参考文献中间体

合成目标

【1】 Tobe, M.; Isobe, Y.; Tomizawa, H.; Nagasaki, T.; Takahashi, H.; Fukazawa, T.; Hayashi, H.; Discovery of quinazolines as a novel structural class of potent inhibitors of NF-kappaB activation. Bioorg Med Chem 2003, 11, 3, 383.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	34444	6-nitro-4(3H)-quinazolinone	C₈H₅N₃O₃	详情	详情
(II)	63327	4-chloro-6-nitroquinazoline	C₈H₄ClN₃O₂	详情	详情
(III)	63328	2-(4-phenoxyphenyl)-1-ethanamine; 4-phenoxyphenethylamine	C₁₄H₁₅NO	详情	详情
(IV)	63329	6-nitro-N-(4-phenoxyphenethyl)-4-quinazolinamine; N-(6-nitro-4-quinazolinyl)-N-(4-phenoxyphenethyl)amine	C₂₂H₁₈N₄O₃	详情	详情

Extended Information