N(4)-(3-bromophenyl)-4,7-quinazolinediamine; N-(7-amino-4-quinazolinyl)-N-(3-bromophenyl)amine -Drug Synthesis Database

【结构式】

【分子编号】19138

【品名】N(4)-(3-bromophenyl)-4,7-quinazolinediamine; N-(7-amino-4-quinazolinyl)-N-(3-bromophenyl)amine

【CA登记号】

【分子式】C₁₄H₁₁BrN₄

【分子量】315.1723

【元素组成】C 53.35% H 3.52% Br 25.35% N 17.78%

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：(IV)

Coupling of chloroquinazoline (I) with 3-bromoaniline (II) in refluxing isopropanol yielded anilinoquinazoline (III). The nitro group was then reduced with Fe dust and AcOH in aqueous ethanol to give amine (IV). Finally, condensation with acrylic acid (V) using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide.HCl (EDC) in DMF provided the target acrylamide.

参考文献中间体

合成目标

【1】 Rewcastle, G.W.; et al.; Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-[(phenylmethyl)amino]- and 4-(phenylamino)quinazolines as potent adenosine 5'-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth f. J Med Chem 1995, 38, 18, 3482.
【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)	19135	4-chloro-7-nitroquinazoline		C₈H₄ClN₃O₂	详情	详情
(II)	19136	3-bromoaniline; 3-bromophenylamine; 3-bromobenzenamine	591-19-5	C₆H₆BrN	详情	详情
(III)	19137	N-(3-bromophenyl)-N-(7-nitro-4-quinazolinyl)amine; N-(3-bromophenyl)-7-nitro-4-quinazolinamine		C₁₄H₉BrN₄O₂	详情	详情
(IV)	19138	N(4)-(3-bromophenyl)-4,7-quinazolinediamine; N-(7-amino-4-quinazolinyl)-N-(3-bromophenyl)amine		C₁₄H₁₁BrN₄	详情	详情
(V)	19139	acrylic acid	79-10-7	C₃H₄O₂	详情	详情

Extended Information