6-bromonicotinic acid -Drug Synthesis Database

【结构式】

【分子编号】63412

【品名】6-bromonicotinic acid

【CA登记号】

【分子式】C₆H₄BrNO₂

【分子量】202.0073

【元素组成】C 35.67% H 2% Br 39.56% N 6.93% O 15.84%

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：(VI)

4-Piperidone ethylene ketal (V) is acylated with 6-bromonicotinic acid (VI) employing 1,1'-carbonyldiimidazole to yield amide (VII). The bromide group of (VII) is then displaced with CuCN in hot DMF producing nitrile (VIII). Finally, condensation between N-acylpiperidone (VIII) and amidine (IV) in refluxing EtOH leads to the target spiro quinazoline.

参考文献中间体

合成目标

【1】 Tinker, A.C.; Beaton, H.G.; Boughton-Smith, N.; Cook, T.R.; Cooper, S.L.; Fraser-Rae, L.; Hallam, K.; Hamley, P.; McInally, T.; Nicholls, D.J.; Pimm, A.D.; Wallace, A.V.; 1,2-Dihydro-4-quinazolinamines: Potent, highly selective inhibitors of inducible nitric oxide synthase which show antiinflammatory activity in vivo. J Med Chem 2003, 46, 6, 913.
【2】 Hamley, P.R.J.; Pimm, A.D.; Tinker, A.C.; Beaton, H.G.; McInally, T. (AstraZeneca plc); Pharmaceutically active quinazoline cpds.. EP 0858451; JP 1999513679; WO 9714686 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	63411	2-amino-3,6-difluorobenzenecarboximidamide		C₇H₇F₂N₃	详情	详情
(V)	11338	1,4-Dioxa-8-azaspiro[4.5]decane; 4-Piperidone ethylene ketal	177-11-7	C₇H₁₃NO₂	详情	详情
(VI)	63412	6-bromonicotinic acid		C₆H₄BrNO₂	详情	详情
(VII)	63413	(6-bromo-3-pyridinyl)(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)methanone		C₁₃H₁₅BrN₂O₃	详情	详情
(VIII)	63414	5-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)-2-pyridinecarbonitrile		C₁₄H₁₅N₃O₃	详情	详情

Extended Information