3-(4-chlorophenoxy)-2,4-pentanedione; 3-(4-chlorophenoxy)pentane-2,4-dione -Drug Synthesis Database

【结构式】

【分子编号】58390

【品名】3-(4-chlorophenoxy)-2,4-pentanedione; 3-(4-chlorophenoxy)pentane-2,4-dione

【CA登记号】

【分子式】C₁₁H₁₁ClO₃

【分子量】226.65924

【元素组成】C 58.29% H 4.89% Cl 15.64% O 21.18%

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)

Condensation of the pyridyl enaminone (I) with thiourea (II) in the presence of NaOEt gives 2-mercapto-4-(pyridin-2-yl)pyrimidine (III), which is alkylated with iodomethane, producing the corresponding methylsulfanyl pyrimidine (IV). Subsequent displacement of the methylsulfanyl group of (IV) with hydrazine leads to the hydrazino pyrimidine (V). Rhodium acetate-catalyzed coupling between 3-diazo-2,4-pentanedione (VI) and 4-chlorophenol (VII) furnishes the chlorophenyl ether (VIII). The tile pyrazole derivative is finally obtained by condensation between hydrazine (V) and diketone (VIII) in the presence of p-toluenesulfonic acid in boiling EtOH.

参考文献中间体

合成目标

【1】 Hirth, B.H.; Kane, J.L. Jr.; Janjigian, A.D.; et al.; Discovery of TNF-alpha induced apoptosis inhibitors with activity in a murine model of multiple sclerosis: Pyrazole series. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 273.
【2】 Hirth, B.H.; Sneddon, S.F.; Kane, J.L.; Vinick, F.; Qiao, S.; Nahill, S.R. (Genzyme Corp.); Modulators of TNF-alpha signaling. WO 0187849 .

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)	58385	(E)-3-(dimethylamino)-1-(2-pyridinyl)-2-propen-1-one		C₁₀H₁₂N₂O	详情	详情
(II)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(III)	58386	4-(2-pyridinyl)-2-pyrimidinylhydrosulfide; 4-(2-pyridinyl)-2-pyrimidinethiol		C₉H₇N₃S	详情	详情
(IV)	58387	2-(methylsulfanyl)-4-(2-pyridinyl)pyrimidine; methyl 4-(2-pyridinyl)-2-pyrimidinyl sulfide		C₁₀H₉N₃S	详情	详情
(V)	58388	2-hydrazino-4-(2-pyridinyl)pyrimidine		C₉H₉N₅	详情	详情
(VI)	58389			C₅H₆N₂O₂	详情	详情
(VII)	35543	4-chlorophenol	106-48-9	C₆H₅ClO	详情	详情
(VIII)	58390	3-(4-chlorophenoxy)-2,4-pentanedione; 3-(4-chlorophenoxy)pentane-2,4-dione		C₁₁H₁₁ClO₃	详情	详情

Extended Information