• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【药物名称】

【化学名称】 

【CA登记号】

【 分 子 式 】C24H26BrN5O3

【 分 子 量 】512.41052

【开发单位】

【药理作用】0

合成路线1

Nitration of quinazolinone (I) with fuming HNO3 in H2SO4 at 100 C gave a mixture of 6-nitro and 8-nitroquinazolines, from which the desired 6-isomer was isolated by recrystallization from AcOH. Subsequent treatment with refluxing SOCl2 and a catalytic amount of DMF gave chloride (III), which was condensed with 3-bromoaniline (IV) in isopropanol to afford anilinoquinazoline (V). Reaction with sodium alkoxide (VI) in refluxing THF provided ether (VII). Then, the nitro group was reduced with Fe dust and AcOH in aqueous ethanol to give amine (VIII). Finally, condensation with acrylic acid (X) using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (EDC) in DMF yielded the target acrylamide.

1 Rewcastle, G.W.; et al.; Tyrosine kinase inhibitors. 9. Synthesis and evaluation of fused tricyclic quinazoline analogues as ATP site inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor. J Med Chem 1996, 39, 4, 918.
2 Dobrusin, E.M.; Bridges, A.J.; Zhou, H.; Smaill, J.B.; Doherty, A.M.; Denny, W.A.; McNamara, D.J.; Showalter, H.D. (Pfizer Inc.); Irreversible inhibitors of tyrosine kinases. JP 2000508657; WO 9738983 .
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) 19140 7-fluoro-4(3H)-quinazolinone C8H5FN2O 详情 详情
(II) 19141 7-fluoro-6-nitro-4(3H)-quinazolinone C8H4FN3O3 详情 详情
(III) 19142 4-chloro-7-fluoro-6-nitroquinazoline C8H3ClFN3O2 详情 详情
(IV) 19136 3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine 591-19-5 C6H6BrN 详情 详情
(V) 19144 N-(3-bromophenyl)-N-(7-fluoro-6-nitro-4-quinazolinyl)amine; N-(3-bromophenyl)-7-fluoro-6-nitro-4-quinazolinamine C14H8BrFN4O2 详情 详情
(VI) 19145 3-(4-Morpholinyl)-1-propanol sodium salt C7H14NNaO2 详情 详情
(VII) 19146 N-(3-bromophenyl)-7-[3-(4-morpholinyl)propoxy]-6-nitro-4-quinazolinamine; N-(3-bromophenyl)-N-[7-[3-(4-morpholinyl)propoxy]-6-nitro-4-quinazolinyl]amine C21H22BrN5O4 详情 详情
(VIII) 19147 N(4)-(3-bromophenyl)-7-[3-(4-morpholinyl)propoxy]-4,6-quinazolinediamine; N-[6-amino-7-[3-(4-morpholinyl)propoxy]-4-quinazolinyl]-N-(3-bromophenyl)amine C21H24BrN5O2 详情 详情
(IX) 19139 acrylic acid 79-10-7 C3H4O2 详情 详情
Extended Information