6-chloro-3-pyridazinamine; 6-chloro-3-pyridazinylamine -Drug Synthesis Database

【结构式】

【分子编号】43962

【品名】6-chloro-3-pyridazinamine; 6-chloro-3-pyridazinylamine

【CA登记号】5469-69-2

【分子式】C₄H₄ClN₃

【分子量】129.54868

【元素组成】C 37.09% H 3.11% Cl 27.37% N 32.44%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(I)

Condensation between 3-amino-6-chloropyridazine (I) and 3-hydroxy-2-methylpyridine (II) in aqueous NaOH at 175 C under pressure afforded the bisaryl ether (III). The phenyl carbamate (IV) was then prepared by treatment of aminopyridazine (III) with phenyl chloroformate. Finally, coupling of carbamate (IV) with 6-chloro-5-methylindoline (V) yielded the title urea derivative.

参考文献中间体

合成目标

【1】 Bromidge, S.M.; Davies, S.; Dabbs, S.; et al.; 1-[2-(Heteroaryloxy)heteroaryl]carbamoy]indolines: Novel and selective 5-HT2C receptor inverse agonists with potential as antidepressant/anxiolytic agents. Bioorg Med Chem Lett 2000, 10, 16, 1863.

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)	43962	6-chloro-3-pyridazinamine; 6-chloro-3-pyridazinylamine	5469-69-2	C₄H₄ClN₃	详情	详情
(II)	29609	2-methyl-3-pyridinol	1121-25-1	C₆H₇NO	详情	详情
(III)	43963	6-[(2-methyl-3-pyridinyl)oxy]-3-pyridazinamine; 6-[(2-methyl-3-pyridinyl)oxy]-3-pyridazinylamine		C₁₀H₁₀N₄O	详情	详情
(IV)	43964	phenyl 6-[(2-methyl-3-pyridinyl)oxy]-3-pyridazinylcarbamate		C₁₇H₁₄N₄O₃	详情	详情
(V)	26798	6-chloro-5-methylindoline		C₉H₁₀ClN	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Imidazopyridazine (III) was prepared by condensation of 3-amino-6-chloropyridazine (I) with ethyl 4-chloroacetoacetate (II) in refluxing ethanol. Alkylation of (III) with iodomethane in the presence of NaH furnished the dimethyl derivative (IV). Alternatively, intermediate (IV) was directly obtained by condensation of 3-amino-6-chloropyridazine (I) with ethyl 4-bromo-2,2-dimethyl-3-oxobutanoate (V) in the presence of disodium phosphate. Reaction of the chloroimidazopyridazine (IV) with 3-[4-(diphenylmethoxy)piperidin-1-yl]propanamine (VI) at 200 C provided adduct (VII). The ethyl ester function of (VII) was finally hydrolyzed to the target carboxylic acid employing NaOH.

参考文献中间体

合成目标

【1】 Gyoten, M.; Kawano, Y.; Nagaya, H. (Takeda Chemical Industries, Ltd.); Condensed pyridazine derivs., their production and use. EP 0979231; JP 1999310581; JP 1999310582; US 6248740; WO 9849167 .

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)	43962	6-chloro-3-pyridazinamine; 6-chloro-3-pyridazinylamine	5469-69-2	C₄H₄ClN₃	详情	详情
(II)	23541	ethyl 4-chloro-3-oxobutanoate；Ethyl 4-chloro-3-oxobutanoate；Ethyl 4-chloroacetoacetate	638-07-3	C₆H₉ClO₃	详情	详情
(III)	47696	ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)acetate		C₁₀H₁₀ClN₃O₂	详情	详情
(IV)	47697	ethyl 2-(6-chloroimidazo[1,2-b]pyridazin-2-yl)-2-methylpropanoate		C₁₂H₁₄ClN₃O₂	详情	详情
(V)	47698	ethyl 4-bromo-2,2-dimethyl-3-oxobutanoate		C₈H₁₃BrO₃	详情	详情
(VI)	47699	3-[4-(benzhydryloxy)-1-piperidinyl]-1-propanamine; 3-[4-(benzhydryloxy)-1-piperidinyl]propylamine		C₂₁H₂₈N₂O	详情	详情
(VII)	47700	ethyl 2-[6-([3-[4-(benzhydryloxy)-1-piperidinyl]propyl]amino)imidazo[1,2-b]pyridazin-2-yl]-2-methylpropanoate		C₃₃H₄₁N₅O₃	详情	详情

Extended Information