SB-414240-药物合成数据库

【药物名称】SB-414240

化学结构式(Chemical Structure):

参考文献No.	43638
标题:	Quinoline derivs. as NK-2 and NK-3 receptor ligands
作者:	Giardina, G.; Grugni, M.; Raveglia, L.F.; Nadler, G.M.M.G.; Farina, C. (SmithKline Beecham SpA)
来源:	EP 1131294; WO 0031038

合成路线图解说明: Esterification of the commercially available carboxylic acid (I) by treatment with oxalyl chloride in DCM followed by reaction with MeOH in CH2Cl2 provides methyl carboxylate (II), which is then brominated with NBS and catalytic dibenzoylperoxide in refluxing acetonitrile to afford 3-bromomethylquinoline derivative (III). Treatment of (III) with secondary amine (IV) and DIEA in THF furnishes compound (V), which is then converted into the desired product by acidic hydrolysis in refluxing HCl followed by coupling with primary amine (VI) by means of HBTU and Et3N in refluxing THF/CH2Cl2.

参考文献No.	616462
标题:	Stepwise modulation of neurokinin-3 and neurokinin-2 receptor affinity and selectivity in quinoline tachykinin receptor antagonists
作者:	Blaney, F.E.; Raveglia, L.F.; Artico, M.; Cavagnera, S.; Dartois, C.; Farina, C.; Grugni, M.; Gagliardi, S.; Luttmann, M.A.; Martinelli, M.J.; Nadler, G.M.; Parini, C.; Petrillo, P.; Sarau, H.M.; Scheideler, M.A.; Hay, D.W.P.; Giardina, G.A.
来源:	J Med Chem 2001,44(11),1675

合成路线图解说明: Esterification of the commercially available carboxylic acid (I) by treatment with oxalyl chloride in DCM followed by reaction with MeOH in CH2Cl2 provides methyl carboxylate (II), which is then brominated with NBS and catalytic dibenzoylperoxide in refluxing acetonitrile to afford 3-bromomethylquinoline derivative (III). Treatment of (III) with secondary amine (IV) and DIEA in THF furnishes compound (V), which is then converted into the desired product by acidic hydrolysis in refluxing HCl followed by coupling with primary amine (VI) by means of HBTU and Et3N in refluxing THF/CH2Cl2.