6-(3-Amino-2-hydroxypropoxy)-2(1H)-quinolinone -Drug Synthesis Database

【结构式】

【分子编号】13915

【品名】6-(3-Amino-2-hydroxypropoxy)-2(1H)-quinolinone

【CA登记号】

【分子式】C₁₂H₁₄N₂O₃

【分子量】234.25484

【元素组成】C 61.53% H 6.02% N 11.96% O 20.49%

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：(III)

6-Hydroxy-2(1H)-quinolinone (I) is alkylated with epichlorohydrin in the presence of K2CO3 in MeOH to afford 6-(2,3-epoxypropoxy)-2(1H)-quinolinone (II). Ring opening of the epoxide (II) with 3,4-dimethoxybenzylamine gives OPC-18790. This compound is also obtained by the reductive alkylation of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone (III) with 3,4-dimethoxybenzaldehyde.

参考文献中间体

合成目标

【1】 Sumida, T.; Fujioka, T.; Teramoto, S.; Tominaga, M.; Yabuuchi, Y.; Mori, T.; Hosokawa, T.; Novel positive inotropic agents; synthesis and biological activities of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone derivatives. J Med Chem 1992, 35, 20, 3607-12.
【2】 Fujioka, T.; OPC-18790. Drugs Fut 1993, 18, 12, 1114.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
	13920	(3,4-Dimethoxyphenyl)methanamine; 3,4-Dimethoxybenzylamine; Veratrylamine	5763-61-1	C₉H₁₃NO₂	详情	详情
	18304	3,4-Dimethoxybenzaldehyde; Veratraldehyde	120-14-9	C₉H₁₀O₃	详情	详情
(I)	13913	6-Hydroxy-2(1H)-quinolinone		C₉H₇NO₂	详情	详情
(II)	13914	6-(2-Oxiranylmethoxy)-2(1H)-quinolinone		C₁₂H₁₁NO₃	详情	详情
(III)	13915	6-(3-Amino-2-hydroxypropoxy)-2(1H)-quinolinone		C₁₂H₁₄N₂O₃	详情	详情

Extended Information