3-(benzyloxy)-2-(1-methoxyethyl)-1,6-dimethyl-4(1H)-pyridinone -Drug Synthesis Database

【结构式】

【分子编号】45938

【品名】3-(benzyloxy)-2-(1-methoxyethyl)-1,6-dimethyl-4(1H)-pyridinone

【CA登记号】

【分子式】C₁₇H₂₁NO₃

【分子量】287.35868

【元素组成】C 71.06% H 7.37% N 4.87% O 16.7%

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：(VII)

Treatment of allomaltol (I) with acetaldehyde (II) and NaOH in H2O affords pyranone derivative (III), which is benzylated by means of benzyl bromide (IV) and NaOH in refluxing H2O/MeOH to provide compound (V). O-Methylation of (V) by reaction with NaH and MeI in DMF furnishes methoxyethyl derivative (VI), which is then heated with methylamine and NaOH in EtOH/H2O to yield pyridinone derivative (VII). Finally, the benzyl group of (VII) is removed by hydrogenation over Pd/C in MeOH to give the desired product.

参考文献中间体

合成目标

【1】 Tilbrook, G.S.; Hider, R.C.; Liu, Z. (BTG International Ltd.); Novel orally active iron (III) chelators. WO 9854138 .

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)	45934	5-hydroxy-2-methyl-4H-pyran-4-one		C₆H₆O₃	详情	详情
(II)	11974	Acetaldehyde	75-07-0	C₂H₄O	详情	详情
(III)	45935	3-hydroxy-2-(1-hydroxyethyl)-6-methyl-4H-pyran-4-one		C₈H₁₀O₄	详情	详情
(IV)	12912	1-(Bromomethyl)benzene; Alpha-bromotoluene	100-39-0	C₇H₇Br	详情	详情
(V)	45936	3-(benzyloxy)-2-(1-hydroxyethyl)-6-methyl-4H-pyran-4-one		C₁₅H₁₆O₄	详情	详情
(VI)	45937	3-(benzyloxy)-2-(1-methoxyethyl)-6-methyl-4H-pyran-4-one		C₁₆H₁₈O₄	详情	详情
(VII)	45938	3-(benzyloxy)-2-(1-methoxyethyl)-1,6-dimethyl-4(1H)-pyridinone		C₁₇H₂₁NO₃	详情	详情

Extended Information