tert-butyl 2-[2-(7-chloro[1,8]naphthyridin-2-yl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetate -Drug Synthesis Database

【结构式】

【分子编号】11336

【品名】tert-butyl 2-[2-(7-chloro[1,8]naphthyridin-2-yl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetate

【CA登记号】

【分子式】C₂₂H₂₀ClN₃O₃

【分子量】409.87192

【元素组成】C 64.47% H 4.92% Cl 8.65% N 10.25% O 11.71%

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：(III)

The reaction of 2-(7-chloro-1,8-naphthyrin-2-yl)-3-hydroxyisoindolin-1-one (I) with tert-butoxycarbonylmethylenetriphenylphosphorane (II) in refluxing toluene gives 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxoisoindolin-1-acetic acid tert-butyl ester (III), which is hydrolyzed with trifluoroacetic acid to the corresponding free acid (IV). Finally, this compound is condensed with 1,4-dioxa-8-azaspiro[4.5]decane (V) by means of diethyl phosphorocyanidate and triethylamine in DMF.

参考文献中间体

合成目标

【1】 Okada, T.; Mohler, M.; Benzodiazepine receptor: Demonstration in the central nervous system. Science 1977, 198, 849-51.
【2】 Goto, G.; Saji, Y. (Takeda Chemical Industries, Ltd.); Isoindolinone derivs., production and use thereof. EP 0174858; JP 1986069773; JP 1990262578; JP 1992364180; US 4778801 .
【3】 Graul, A.; Prous, J.; Castaner, J.; DN-2327. Drugs Fut 1993, 18, 5, 414.

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)	11334	2-(7-Chloro[1,8]naphthyridin-2-yl)-3-hydroxy-1-isoindolinone		C₁₆H₁₀ClN₃O₂	详情	详情
(II)	11335	tert-butyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (tert-Butoxycarbonylmethylene)triphenylphosphorane	35000-38-5	C₂₄H₂₅O₂P	详情	详情
(III)	11336	tert-butyl 2-[2-(7-chloro[1,8]naphthyridin-2-yl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetate		C₂₂H₂₀ClN₃O₃	详情	详情
(IV)	11337	2-[2-(7-chloro[1,8]naphthyridin-2-yl)-3-oxo-2,3-dihydro-1H-isoindol-1-yl]acetic acid		C₁₈H₁₂ClN₃O₃	详情	详情
(V)	11338	1,4-Dioxa-8-azaspiro[4.5]decane; 4-Piperidone ethylene ketal	177-11-7	C₇H₁₃NO₂	详情	详情

Extended Information