3-[(1S)-1-(2-fluoro[1,1'-biphenyl]-4-yl)ethyl]-5-isoxazolamine; 3-[(1S)-1-(2-fluoro[1,1'-biphenyl]-4-yl)ethyl]-5-isoxazolylamine -Drug Synthesis Database

【结构式】

【分子编号】52009

【品名】3-[(1S)-1-(2-fluoro[1,1'-biphenyl]-4-yl)ethyl]-5-isoxazolamine; 3-[(1S)-1-(2-fluoro[1,1'-biphenyl]-4-yl)ethyl]-5-isoxazolylamine

【CA登记号】

【分子式】C₁₇H₁₅FN₂O

【分子量】282.3173832

【元素组成】C 72.33% H 5.36% F 6.73% N 9.92% O 5.67%

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：(IV)

The condensation of 2(S)-(2-fluorobiphenyl-4-yl)propionic acid (I) with tert-butyl cyanacetate (II) by means of lithium amide in THF gives lithium enolate (III), which is cyclized with hydroxylamine in aqueous DMF to yield the 5-aminoisoxazole (IV). Finally, this compound is condensed with morpholine-4-carbonitrile by means of lithium amide in toluene/tert-butanol to afford the target amidine.

参考文献中间体

合成目标

【1】 Nakatsuka, M.; et al.; Novel disease modifying anti-rheumatic agents (DMARDs): Syntheses and SAR of 5-guanidinoisoxazoles. 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 269.
【2】 Ueno, Y.; Okada, S.; Nakatsuka, M.; Nishikaku, F. (Sumitomo Pharmaceuticals Co., Ltd.); Isoxazole derivs.. EP 0979226; JP 1999240873; US 6100260; WO 9847880 .

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)	52007	(2S)-2-(2-fluoro[1,1'-biphenyl]-4-yl)propionic acid		C₁₅H₁₃FO₂	详情	详情
(II)	14330	tert-Butyl cyanoacetate; tert-butyl 2-cyanoacetate	1116-98-9	C₇H₁₁NO₂	详情	详情
(III)	52008			C₂₂H₂₁FLiNO₃	详情	详情
(IV)	52009	3-[(1S)-1-(2-fluoro[1,1'-biphenyl]-4-yl)ethyl]-5-isoxazolamine; 3-[(1S)-1-(2-fluoro[1,1'-biphenyl]-4-yl)ethyl]-5-isoxazolylamine		C₁₇H₁₅FN₂O	详情	详情
(V)	52010	4-Morpholinecarbonitrile; Morpholine-4-carbonitrile; N-Cyanomorpholine	1530-89-8	C₅H₈N₂O	详情	详情

Extended Information