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【结 构 式】

【分子编号】35969

【品名】3-chloro-6-[3-(trifluoromethyl)phenyl]pyridazine

【CA登记号】

【 分 子 式 】C11H6ClF3N2

【 分 子 量 】258.6300296

【元素组成】C 51.08% H 2.34% Cl 13.71% F 22.04% N 10.83%

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:(VIII)

The reaction of 3-trifluoromethylbenzaldehyde (I) with morpholine (II) and potassium cyanide by means of p-toluenesulfonic acid in refluxing THF gives alpha-(3-trifluoromethylphenyl)-4-morpholineacetonitrile (III), which is condensed with ethyl acrylate (IV) by means of KOH in THF yielding gamma-cyano-gamma-(3-trifluoromethylphenyl)-4-morpholinebutyric acid ethyl ester (V). The cyclization of (V) with hydrazine in refluxing ethanol affords 4,5-dihydro-6-(3-trifluoromethylphenyl)-3(2H)-pyridazinone (VI), which is dehydrogenated by treatment with Br2 in hot acetic acid to give 6-(3-trifluoromethylphenyl)-3(2H)-pyridazinone (VII). The reaction of (VII) with POCl3 at 100 C affords 3-chloro-6-(3-trifluoromethylphenyl)pyridazine (VIII), which is finally cyclized with acetylhydrazine (IX) in refluxing n-butanol.

1 Allen, G.R. Jr.; Hanifin, J.W. Jr.; Moran, D.B.; Albright, J.D.; 6-Phenyl-1,2,4-triazolo{8 4,3-b{9 pyridazine hypotensive agents. US 4112095 .
2 Albright, J.D.; et al.; Synthesis and anxiolytic activity of 6-(substituted-phenyl)-1,2,4-triazolo[4,3-b]pyridazines. J Med Chem 1981, 24, 5, 592-600.
3 Owen, R.T.; Serradell, M.N.; Blancafort, P.; Castaner, J.; CL-218,872. Drugs Fut 1983, 8, 3, 191.
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) 35964 3-(trifluoromethyl)benzaldehyde 454-89-7 C8H5F3O 详情 详情
(II) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(III) 35965 2-(4-morpholinyl)-2-[3-(trifluoromethyl)phenyl]acetonitrile C13H13F3N2O 详情 详情
(IV) 10164 ethyl acrylate 140-88-5 C5H8O2 详情 详情
(V) 35966 ethyl 4-cyano-4-(4-morpholinyl)-4-[3-(trifluoromethyl)phenyl]butanoate C18H21F3N2O3 详情 详情
(VI) 35937 3-amino-6-chloro-4-phenyl-3,4-dihydro-4-quinazolinol C14H12ClN3O 详情 详情
(VII) 35968 6-[3-(trifluoromethyl)phenyl]-3(2H)-pyridazinone C11H7F3N2O 详情 详情
(VIII) 35969 3-chloro-6-[3-(trifluoromethyl)phenyl]pyridazine C11H6ClF3N2 详情 详情
(IX) 29262 acetohydrazide 1068-57-1 C2H6N2O 详情 详情
Extended Information