2-[3-(cyclopentyloxy)-4-methoxyphenyl]-5-nitro-1H-isoindole-1,3(2H)-dione -Drug Synthesis Database

【结构式】

【分子编号】64275

【品名】2-[3-(cyclopentyloxy)-4-methoxyphenyl]-5-nitro-1H-isoindole-1,3(2H)-dione

【CA登记号】

【分子式】C₂₀H₁₈N₂O₆

【分子量】382.3728

【元素组成】C 62.82% H 4.74% N 7.33% O 25.11%

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：(VI)

Alkylation of 2-methoxy-5-nitrophenol (I) with cyclopentyl bromide (II) provides the cyclopentyl ether (III). Subsequent reduction of the nitro derivative (III) to aniline (IV) is effected by transfer hydrogenation in the presence of ammonium formate and Pd/C. Condensation of 3-(cyclopentyloxy)-4-methoxyaniline (IV) with 4-nitrophthalic anhydride (V) gives rise to phthalimide (VI). Reduction of imide (VI) by means of NaBH4 furnishes the amide alcohol (VII), which is further cyclized to isoindoline (VIII) under Mitsunobu conditions. Finally, transfer hydrogenation of nitro isoindoline (VIII) gives rise to the corresponding amine.

参考文献中间体

合成目标

【1】 Park, J.S.; Moon, S.C.; Baik, K.U.; Cho, J.Y.; Yoo, E.S.; Byun, Y.S.; Park, M.H.; Synthesis and SAR studies for the inhibition of TNF-alpha production. Part 2. 2-[3-(Cyclopentyloxy)-4-methoxyphenyl]-substituted-1-isoindolinone derivatives. Arch Pharmacal Res 2002, 25, 2, 137.

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)	64272	2-methoxy-5-nitrophenol		C₇H₇NO₄	详情	详情
(II)	10972	1-Bromocyclopentane; Cyclopentyl bromide	137-43-9	C₅H₉Br	详情	详情
(III)	64273	cyclopentyl 2-methoxy-5-nitrophenyl ether; 2-(cyclopentyloxy)-1-methoxy-4-nitrobenzene		C₁₂H₁₅NO₄	详情	详情
(IV)	64274	3-(cyclopentyloxy)-4-methoxyphenylamine; 3-(cyclopentyloxy)-4-methoxyaniline		C₁₂H₁₇NO₂	详情	详情
(V)	31028	5-nitro-2-benzofuran-1,3-dione	5466-84-2	C₈H₃NO₅	详情	详情
(VI)	64275	2-[3-(cyclopentyloxy)-4-methoxyphenyl]-5-nitro-1H-isoindole-1,3(2H)-dione		C₂₀H₁₈N₂O₆	详情	详情
(VII)	64276	N-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-(hydroxymethyl)-5-nitrobenzamide		C₂₀H₂₂N₂O₆	详情	详情
(VIII)	64277	2-[3-(cyclopentyloxy)-4-methoxyphenyl]-6-nitro-1-isoindolinone		C₂₀H₂₀N₂O₅	详情	详情

Extended Information