3-chloro-6-phenylpyridazine -Drug Synthesis Database

【结构式】

【分子编号】31451

【品名】3-chloro-6-phenylpyridazine

【CA登记号】

【分子式】C₁₀H₇ClN₂

【分子量】190.63176

【元素组成】C 63.01% H 3.7% Cl 18.6% N 14.7%

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)

Horner-Emmons reaction of 1-benzyl-4-piperidone (I) with diethyl cyanomethylphosphonate (II) in the presence of K2CO3 provided the piperidinilydeneacetonitrile (III). Reduction of the double bond of (III) with magnesium in MeOH yielded the saturated nitrile (IV), which was further reduced to amine (V) using LiAlH4. Treatment of 6-phenyl-3-pyridazinone (VI) with POCl3 gave the chloropyridazine (VII). This was coupled with diamine (V) in the presence of ammonium chloride in refluxing butanol to furnish the title pyridazinamine, which was finally converted to the dihydrochloride salt.

参考文献中间体

合成目标

【1】 Rival, Y.M.; Bourguignon, J.-J.; Contreras, J.-M.; Chayer, S.; Wermuth, C.G.; Aminopyridazines as acetylcholinesterase inhibitors. J Med Chem 1999, 42, 4, 730.

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)	15720	1-benzyltetrahydro-4(1H)-pyridinone; 1-Benzyl-4-piperidone; N-Benzyl-4-piperidone; 1-(benzyl)-4-piperidinone; 1-benzylpiperidin-4-one; 1-(benzyl)piperidin-4-one	3612-20-2	C₁₂H₁₅NO	详情	详情
(II)	10045	Diethyl cyanomethylphosphonate	2537-48-6	C₆H₁₂NO₃P	详情	详情
(III)	31448	2-(1-benzyl-4-piperidinylidene)acetonitrile		C₁₄H₁₆N₂	详情	详情
(IV)	31449	2-(1-benzyl-4-piperidinyl)acetonitrile		C₁₄H₁₈N₂	详情	详情
(V)	17606	2-(1-benzyl-4-piperidinyl)-1-ethanamine; 2-(1-benzyl-4-piperidinyl)ethylamine		C₁₄H₂₂N₂	详情	详情
(VI)	31450	6-phenyl-3(2H)-pyridazinone		C₁₀H₈N₂O	详情	详情
(VII)	31451	3-chloro-6-phenylpyridazine		C₁₀H₇ClN₂	详情	详情

Extended Information