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【结 构 式】

【分子编号】64007

【品名】2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-(3-nitrophenyl)nicotinonitrile

【CA登记号】

【 分 子 式 】C24H26N4O3Si

【 分 子 量 】446.5811

【元素组成】C 64.55% H 5.87% N 12.55% O 10.75% Si 6.29%

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)

2'-Hydroxyacetophenone (I) is protected as the silyl ether (II) employing t-butyldimethylsilyl chloride and imidazole. Condensation of acetophenone (II) with 3-nitrobenzaldehyde (III) and malononitrile in the presence of ammonium acetate gives rise to the cyanopyridine (IV). The nitro group of (IV) is then reduced to the corresponding amine (V) by catalytic hydrogenation over Pd/C. 3-Piperidinylpropionic acid (VI) is then activated as the acid chloride (VII) upon treatment with oxalyl chloride. Subsequent coupling of acid chloride (VII) with amine (V) furnishes amide (VIII). Finally, desilylation of (VIII) by means of either tetrabutylammonium fluoride or HCl in dioxane leads to the title compound. (1,2)

1 Murata, T.; Shimada, M.; Sakakibara, S.; Yoshino, T.; Kadono, H.; Masuda, T.; Shimazaki, M.; Shintani, T.; Fuchikami, K.; Sakai, K.; Inbe, H.; Takeshita, K.; Niki, T.; Umeda, M.; Bacon, K.B.; Ziegelbauer, K.B.; Lowinger, T.B.; Discovery of novel and selective IKK-beta serine-threonine protein kinase inhibitors. Part 1. Bioorg Med Chem Lett 2003, 13, 5, 913.
2 Yoshida, N.; Masuda, T.; Sakakibara, S.; Murata, T.; Yoshino, T.; Umeda, M.; Shimada, M.; Lowinger, T.B.; Komura, H.; Shintani, T.; Ziegelbauer, K.B.; Fuchikami, K.; Ikegami, Y.; Shimazaki, M. (Bayer AG); 4-Aryl pyridine derivs.. EP 1339687; JP 2002193938; WO 0244153 .
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) 29654 2-hydroxyacetophenone; 1-(2-hydroxyphenyl)-1-ethanone 118-93-4 C8H8O2 详情 详情
(II) 64006 1-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-ethanone C14H22O2Si 详情 详情
(III) 12646 3-Nitrobenzaldehyde 99-61-6 C7H5NO3 详情 详情
(IV) 64007 2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-(3-nitrophenyl)nicotinonitrile C24H26N4O3Si 详情 详情
(V) 64008 2-amino-4-(3-aminophenyl)-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)nicotinonitrile C24H28N4OSi 详情 详情
(VI) 64010 3-(1-piperidinyl)propanoic acid C8H15NO2 详情 详情
(VII) 64011 3-(1-piperidinyl)propanoyl chloride C8H14ClNO 详情 详情
(VIII) 64009 N-{3-[2-amino-6-(2-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-cyano-4-pyridinyl]phenyl}-3-(1-piperidinyl)propanamide C32H41N5O2Si 详情 详情
Extended Information