　 -Drug Synthesis Database

【结构式】

【分子编号】37091

【品名】　

【CA登记号】

【分子式】C₇H₅Cl₂FNO₂P

【分子量】255.9998052

【元素组成】C 32.84% H 1.97% Cl 27.7% F 7.42% N 5.47% O 12.5% P 12.1%

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：(II)

The reaction of p-fluorobenzamide (I) with phosphorus pentachloride (II) in refluxing CCl4, followed by a treatment with formic acid gives N-(dichlorophosphinyl)-p-fluorobenzamide (III), which is then treated with NH3 in CHCl3.

参考文献中间体

合成目标

【1】 Blancafort, P.; Castaner, J.; Serradell, M.N.; Flurofamide. Drugs Fut 1982, 7, 10, 734.
【2】 Bayless, A.V.; Millner, O.E. Jr. (Norwich Eaton); N-[Diaminophosphinyl]arylcarboxamides. US 4182881 .

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)	37090	4-fluorobenzamide	824-75-9	C₇H₆FNO	详情	详情
(II)	37091			C₇H₅Cl₂FNO₂P	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The synthesis of the intermediate (chlorophenyl)piperazinone (VIII) has been reported by two procedures. The hydrochloride salt prepared from 3-chloroaniline (I) was treated with 2-oxazolidinone (II) at 160 C to produce the aryl ethylenediamine (III), which was subsequently protected as the N-Boc derivative (IV). Acylation of aniline (IV) with chloroacetyl chloride (V) gave the chloroacetamide (VI). This was then cyclized to the piperazinone (VII) by treatment with K2CO3 in hot DMF. Further acid deprotection of the Boc group of (VII) afforded the intermediate (VIII).

参考文献中间体

合成目标

【1】 Anthony, N.J.; Ciccarone, T.M.; Gomez, R.P.; Hutchinson, J.H.; Williams, T.M.; Dinsmore, C.J.; Stokker, G.E. (Merck & Co., Inc.); Inhibitors of farnesyl-protein transferase. EP 0820445; JP 1998511098; US 5856326; WO 9630343 .
【2】 Williams, T.M.; Dinsmore, C.J.; Hutchinson, J.H. (Merck & Co., Inc.); Inhibitors of prenyl-protein transferase. EP 1014984; WO 9909985 .

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)	25239	3-chloroaniline; 3-chlorophenylamine	108-42-9	C₆H₆ClN	详情	详情
(II)	21456	1,3-oxazolidin-2-one	497-25-6	C₃H₅NO₂	详情	详情
(III)	37091			C₇H₅Cl₂FNO₂P	详情	详情
(IV)	47286	tert-butyl 2-(3-chloroanilino)ethylcarbamate		C₁₃H₁₉ClN₂O₂	详情	详情
(V)	11296	2-Chloroacetyl chloride; Chloroacetic chloride	79-04-9	C₂H₂Cl₂O	详情	详情
(VI)	47287	tert-butyl 2-[3-chloro(2-chloroacetyl)anilino]ethylcarbamate		C₁₅H₂₀Cl₂N₂O₃	详情	详情
(VII)	47288	tert-butyl 4-(3-chlorophenyl)-3-oxo-1-piperazinecarboxylate		C₁₅H₁₉ClN₂O₃	详情	详情
(VIII)	47289	1-(3-chlorophenyl)-2-piperazinone		C₁₀H₁₁ClN₂O	详情	详情

Extended Information