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【结 构 式】

【药物名称】Clofurenadine hydrochloride, (?-BN-1267

【化学名称】(±)-3-(4-Chlorophenyl)-1,3-dihydro-3,6-dimethylfuro[3,4-c]pyridin-7-ol hydrochloride

【CA登记号】91868-84-7 (free base)

【 分 子 式 】C15H15Cl2NO2

【 分 子 量 】312.1983

【开发单位】Institut Henri Beaufour (Originator)

【药理作用】Histamine H1 Antagonists

合成路线1

The synthesis of (rac)-BN-1267 is presented. The Grignard reaction of 2,2,8-trimethyl-5-formylpyrido[4,3-e]-1,3-dioxane (I) with 4-chloro phenyl magnesium bromide in refluxing ether gives 2,2,8-trimethyl-5-(4-chloro-alpha-hydroxybenzyl)pyrido[4,3-e]-1,3-dioxane (II), which by oxidation with MnO2 affords the corresponding ketone (III). The Grignard reaction of (III) with methyl maynesium iodide gives 2,2,8-trimethyl-5-(4-chloro-alpha-methyl-alpha-hydraxybenzyl)pyrido[4,3-e]-1,3-dioxane (IV), which is then hydrolyzed and cyclized by treatment with aqueous concentrated HCl.

1 De Salvia, R.; et al.; J Meet Franco-Ital Pharmacol Soc (June, Paris) 1984, 135, 1-2, 1.
2 Esanu, A. (SCRAS (Societé de Conseils de Recherches et d'Applications Scientifiques)); Furo[3,4-c]pyridine derivatives and therapeutic compositions containing the same. BE 0899222; CH 660191; GB 2137618; JP 1984193888; US 4581363; US 4735950 .
3 Esanu, A.; Etienne, A.; Laurent, J.-P.; Braquet, P.; Mencia Huerta, J.M. Clostre, F.; Touvay, C.; Clofurenadine hydrochloride. Drugs Fut 1987, 12, 7, 627.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 25127 bromo(4-chlorophenyl)magnesium 873-77-8 C6H4BrClMg 详情 详情
(I) 28771 2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridine-5-carbaldehyde C11H13NO3 详情 详情
(II) 28772 (3-chlorophenyl)(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol C17H18ClNO3 详情 详情
(III) 28773 (3-chlorophenyl)(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanone C17H16ClNO3 详情 详情
(IV) 28774 1-(3-chlorophenyl)-1-(2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)-1-ethanol C18H20ClNO3 详情 详情
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