1,7,7-trimethylbicyclo[2.2.1]heptan-2-one N-(6-chloro-3-pyridazinyl)hydrazone -Drug Synthesis Database

【结构式】

【分子编号】28923

【品名】1,7,7-trimethylbicyclo[2.2.1]heptan-2-one N-(6-chloro-3-pyridazinyl)hydrazone

【CA登记号】

【分子式】C₁₄H₁₉ClN₄

【分子量】278.78452

【元素组成】C 60.32% H 6.87% Cl 12.72% N 20.1%

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：(IV)

Heating of 3,6-dichloropyridazine (I) with hydrazine hydrate at 100 C gives 6-chloro-3-pyridazinylhydrazine (II). The hydrazino group is protected by transforming it with camphor (III) to the camphorhydrazone (IV), which is aminated by heating with morpholine to give the morpholinylhydrazone (V). After liberating the hydrazine function by acidic hydrolysis in a biphasic system, the resulting 6-morpholino-3-pyridazinylhydrazine (VI) is reacted either with tert-butylacetoacetate (VII) or with tert-butylpropiolate (VIII) to yield RGH-5526.

参考文献中间体

合成目标

【1】 Inoue, H.; Yoshida, M.; Aizawa, H.; et al.; Eur J Med Chem 1984, 19, 6, 111-117.
【2】 Szilagyi, G.; et al. (Gedeon Richter Ltd.); Morpholino pyridazinylhydrazones. DE 2825861; FR 2394535; GB 2000125; HU 176972; JP 54016486; US 4259328; US 4308386 .
【3】 Nogradi, M.; RGH-5526. Drugs Fut 1985, 10, 1, 32.

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)	10388	Morpholine	110-91-8	C₄H₉NO	详情	详情
(I)	11292	3,6-Dichloropyridazine	141-30-0	C₄H₂Cl₂N₂	详情	详情
(II)	28922	3-chloro-6-hydrazinopyridazine	17284-97-8	C₄H₅ClN₄	详情	详情
(III)	28926	1,7,7-trimethylbicyclo[2.2.1]heptan-2-one	464-48-2	C₁₀H₁₆O	详情	详情
(IV)	28923	1,7,7-trimethylbicyclo[2.2.1]heptan-2-one N-(6-chloro-3-pyridazinyl)hydrazone		C₁₄H₁₉ClN₄	详情	详情
(V)	28924	1,7,7-trimethylbicyclo[2.2.1]heptan-2-one N-[6-(4-morpholinyl)-3-pyridazinyl]hydrazone		C₁₈H₂₇N₅O	详情	详情
(VI)	24847	4-(6-hydrazino-3-pyridazinyl)morpholine		C₈H₁₃N₅O	详情	详情
(VII)	27907	Acetoacetic acid tert-butyl ester;3-Oxo-butanoic acid 1,1-dimethylethyl estertert-butyl 3-oxobutanoate	1694-31-1	C₈H₁₄O₃	详情	详情
(VIII)	28925	tert-butyl propiolate	13831-03-3	C₇H₁₀O₂	详情	详情

Extended Information