(E)-3-(dimethylamino)-1-[4-(4-fluorophenyl)-1-(2,2,6,6-tetramethyl-4-piperidinyl)-1H-imidazol-5-yl]-2-propen-1-one -Drug Synthesis Database

【结构式】

【分子编号】25601

【品名】(E)-3-(dimethylamino)-1-[4-(4-fluorophenyl)-1-(2,2,6,6-tetramethyl-4-piperidinyl)-1H-imidazol-5-yl]-2-propen-1-one

【CA登记号】

【分子式】C₂₃H₃₁FN₄O

【分子量】398.5239032

【元素组成】C 69.32% H 7.84% F 4.77% N 14.06% O 4.01%

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：(XVI)

A new procedure, which avoided the unstable pyrimidine aldehye (X), started by condensing pyruvic aldehyde (XIII) with aminopiperidine (XI). The resulting imine (XIV) was reacted with tosyl isonitrile (V) to form the acetyl imidazole (XV). Subsequent treatment of (XV) with N,N-dimethylformamide dimethyl acetal gave enaminoketone (XVI), which was then condensed with guanidine (VIII) to produce the required pyrimidine ring.

参考文献中间体

合成目标

【1】 Sisko, J.; A one-pot synthesis of 1-(2,2,6,6-tetramethyl-4-piperidinyl)-4-(4-fluorophenyl)-5-(2-amino-4-pyrimidinyl)imidazole: A potent inhibitor of P38 MAP kinase. J Org Chem 1998, 63, 13, 4529.
【2】 Sisko, J. (SmithKline Beecham plc); Novel synthesis. US 5917043; WO 9723479 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	25595	4-Fluoro-alpha-(4-methylphenylsulfonyl)benzyl isocyanide		C₁₅H₁₂FNO₂S	详情	详情
(VIII)	14790	Guanidine	113-00-8	CH₅N₃	详情	详情
(XI)	25596	2,2,6,6-tetramethyl-4-piperidinamine	36768-62-4	C₉H₂₀N₂	详情	详情
(XIII)	25598	2-oxopropanal	78-98-8	C₃H₄O₂	详情	详情
(XIV)	25599	1-[(2,2,6,6-tetramethyl-4-piperidinyl)imino]acetone		C₁₂H₂₂N₂O	详情	详情
(XV)	25600	1-[4-(4-fluorophenyl)-1-(2,2,6,6-tetramethyl-4-piperidinyl)-1H-imidazol-5-yl]-1-ethanone		C₂₀H₂₆FN₃O	详情	详情
(XVI)	25601	(E)-3-(dimethylamino)-1-[4-(4-fluorophenyl)-1-(2,2,6,6-tetramethyl-4-piperidinyl)-1H-imidazol-5-yl]-2-propen-1-one		C₂₃H₃₁FN₄O	详情	详情

Extended Information