(E)-3-(6-chloro-3-pyridinyl)-N-methyl-3-phenyl-2-propenamide -Drug Synthesis Database

【结构式】

【分子编号】30807

【品名】(E)-3-(6-chloro-3-pyridinyl)-N-methyl-3-phenyl-2-propenamide

【CA登记号】

【分子式】C₁₅H₁₃ClN₂O

【分子量】272.7338

【元素组成】C 66.06% H 4.8% Cl 13% N 10.27% O 5.87%

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：(V)

Ketone (III) was prepared by Friedel-Crafts acylation of benzene (II) with 6-chloronicotinyl chloride (I). Horner-Emmons reaction of (III) with diethyl (N-methylcarbamoylmethyl)phosphonate (IV) using potassium hexamethyl-disilazide produced a 3:1 mixture of E (V) and Z olefins (VI). The desired E isomer (V) was isolated by column chromatography and then treated with bromoketone (VII) to afford the betaine (VIII). Finally, the target imidazopyridine was obtained by condensation of (VIII) with cyanamide in the presence of K2CO3.

参考文献中间体

合成目标

【1】 Alvarez-Builla, J.; Ezquerra, J.; Vega, J.A.; Vaquero, J.J.; Hamdouchi, C.; Heinz, B.A.; Short synthesis and anti-rhinoviral activity of imidazo[1,2-a]pyridines: The effect of acyl groups at 3-position. Bioorg Med Chem Lett 1999, 9, 10, 1391.

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)	30256	6-chloronicotinoyl chloride	58757-38-3	C₆H₃Cl₂NO	详情	详情
(II)	13364	Benzene	71-43-2	C₆H₆	详情	详情
(III)	30257	(6-chloro-3-pyridinyl)(phenyl)methanone		C₁₂H₈ClNO	详情	详情
(IV)	30262	diethyl 2-(methylamino)-2-oxoethylphosphonate		C₇H₁₆NO₄P	详情	详情
(V)	30807	(E)-3-(6-chloro-3-pyridinyl)-N-methyl-3-phenyl-2-propenamide		C₁₅H₁₃ClN₂O	详情	详情
(VI)	30808	(Z)-3-(6-chloro-3-pyridinyl)-N-methyl-3-phenyl-2-propenamide		C₁₅H₁₃ClN₂O	详情	详情
(VII)	30809	1-bromo-3,3-dimethyl-2-butanone	5469-26-1	C₆H₁₁BrO	详情	详情
(VIII)	30810	1-[2-Chloro-5-[2-(N-metylcarbamoyl)-1-phenylvinyl]pyridinium-1-yl]-3,3-dimethyl-2-oxo-1-butanide		C₂₁H₂₃ClN₂O₂	详情	详情

Extended Information