1-(2,4-dichlorophenyl)-1-ethanone; 2',4'-dichloroaetophenone -Drug Synthesis Database

【结构式】

【分子编号】36407

【品名】1-(2,4-dichlorophenyl)-1-ethanone; 2',4'-dichloroaetophenone

【CA登记号】2234-16-4

【分子式】C₈H₆Cl₂O

【分子量】189.04044

【元素组成】C 50.83% H 3.2% Cl 37.51% O 8.46%

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：(X)

The bromination of 2,4-dichloroacetophenone (X) with Br2 in refluxing methanol gives 2,4-dichlorophenacyl bromide (XI), which is condensed with 1H-imidazole (IX) in methanol to yield 2,4-dichloro-alpha-(1-imidazolyl)acetophenone (XII). The reduction of (XII) with NaBH4 in refluxing methanol affords 1-(2,4-chlorophenyl)-2-(1-imidazolyl)ethanol (XIII), which is finally alkylated with allyl chloride (IV) and NaH in refluxing DMF.

参考文献中间体

合成目标

【1】 Serradell, M.N.; Blancafort, P.; Castaner, J.; de Angelis, L.; Imazalil. Drugs Fut 1982, 7, 4, 254.
【2】 Godefroi, E.F.; Schuermans, J.L.; US 3658813 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	13235	Allyl chloride; 3-Chloro-1-propene	107-05-1	C₃H₅Cl	详情	详情
(IX)	10255	Imidazole; 1H-Imidazole	288-32-4	C₃H₄N₂	详情	详情
(X)	36407	1-(2,4-dichlorophenyl)-1-ethanone; 2',4'-dichloroaetophenone	2234-16-4	C₈H₆Cl₂O	详情	详情
(XI)	36408	2-bromo-1-(2,4-dichlorophenyl)-1-ethanone		C₈H₅BrCl₂O	详情	详情
(XII)	32200	1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanone	46503-52-0	C₁₁H₈Cl₂N₂O	详情	详情
(XIII)	14550	1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-1-ethanol; alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol; 1-(2',4'-Dichlorophenyl)-2-(1-imidazolyl)ethanol	24155-42-8	C₁₁H₁₀Cl₂N₂O	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

Reaction of 2-ethyl-1-bromohexane (I) with potassium cyanide afforded nitrile (II). Claisen condensation of ethyl propionate with nitrile (II) in the presence of LDA furnished keto nitrile (III), which was further cyclized to the pyrazole (IV) upon treatment with hydrazine. Treatment of 2',4'-dichloroacetophenone (V) with dimethylformamide dimethylacetal gave rise to the enamino ketone (VI). The title pyrazolopyrimidine was then obtained by condensation between aminopyrazole (IV) and enamino ketone (VI) in refluxing HOAc.

参考文献中间体

合成目标

【1】 Wilde, R.G.; Gilligan, P.J.; Olson, R.E.; Zaczek, R.; Carter, K.L.; Klaczkiewicz, J.D.; Non-peptide CRF1 antagonists: Pyrazolo[1,5-a]pyrimidines and pyrazolo[5,1-c][1,2,3]triazines. 221st ACS Natl Meet (April 1 2001, San Diego) 2001, Abst MEDI 95.
【2】 Gilligan, P.J.; Wilde, R.G. (DuPont Pharmaceuticals Co.); Pyrazolopyrimidines as CRF antagonists. WO 0059908 .

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)	49775	3-(Bromomethyl)heptane; 1-Bromo-2-Ethylhexane; DL-1-Bromo-2-Ethylhexane; 2-Ethylhexyl bromide	18908-66-2	C₈H₁₇Br	详情	详情
(II)	49776	3-Ethylheptanitrile		C₉H₁₇N	详情	详情
(III)	49777	3-ethyl-2-propionylheptanenitrile		C₁₂H₂₁NO	详情	详情
(IV)	49778	3-ethyl-4-(1-ethylpentyl)-1H-pyrazol-5-amine; 3-ethyl-4-(1-ethylpentyl)-1H-pyrazol-5-ylamine		C₁₂H₂₃N₃	详情	详情
(V)	49779	(E)-1-(2,4-dichlorophenyl)-3-(dimethylamino)-2-propen-1-one		C₁₁H₁₁Cl₂NO	详情	详情
(VI)	36407	1-(2,4-dichlorophenyl)-1-ethanone; 2',4'-dichloroaetophenone	2234-16-4	C₈H₆Cl₂O	详情	详情

Extended Information