ethyl 1-cyclopropyl-8-(2,2-difluoroethyl)-7-[(1R)-1-methyl-2-trityl-2,3-dihydro-1H-isoindol-5-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】61572

【品名】ethyl 1-cyclopropyl-8-(2,2-difluoroethyl)-7-[(1R)-1-methyl-2-trityl-2,3-dihydro-1H-isoindol-5-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate

【CA登记号】

【分子式】C₄₅H₄₀F₂N₂O₃

【分子量】694.8210864

【元素组成】C 77.79% H 5.8% F 5.47% N 4.03% O 6.91%

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：(V)

The reaction of 5-bromo-1(R)-methyl-2-(triphenylmethyl)-2,3-dihydro-1H-isoindole (I) with; BuLi, triisopropyl borate and diethanolamine (II) gives the boronic ester (III), which is condensed with 1-cyclopropyl-7-bromo-8-(difluoromethoxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (IV) by means of PdCl2(PPh3)2 to yield the precursor (V). Finally, this compound is deprotected by a treatment with HCl in ethanol/water to provide the target Garenoxacin.

参考文献中间体

合成目标

【1】 Hayashi, K.; Takahata, M.; Kawamura, Y.; Todo, Y.; Synthesis, antibacterial activity, and toxicity of 7-(isoindolin-5-yl)-4-oxoquinoline-3-carboxylic acids. Discovery of the novel des-F(6)-quinolone antibacterial agent garenoxacin (T-3811 or BMS-284756). Arzneim Forsch Drug Res. 2002, 52, 12, 903.

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)	30634	(1R)-5-bromo-1-methyl-2-trityl-2,3-dihydro-1H-isoindole		C₂₈H₂₄BrN	详情	详情
(II)	24273	2-[(2-hydroxyethyl)amino]-1-ethanol	111-42-2	C₄H₁₁NO₂	详情	详情
(III)	61570	(1R)-5-(1,3,6,2-dioxazaborocan-2-yl)-1-methyl-2-trityl-2,3-dihydro-1H-isoindole		C₃₂H₃₃BN₂O₂	详情	详情
(IV)	61571	ethyl 7-bromo-1-cyclopropyl-8-(2,2-difluoroethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate		C₁₇H₁₆BrF₂NO₃	详情	详情
(V)	61572	ethyl 1-cyclopropyl-8-(2,2-difluoroethyl)-7-[(1R)-1-methyl-2-trityl-2,3-dihydro-1H-isoindol-5-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate		C₄₅H₄₀F₂N₂O₃	详情	详情

Extended Information