tert-butyl 4-(2-methoxy-5-nitrophenyl)-1-piperazinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】25385

【品名】tert-butyl 4-(2-methoxy-5-nitrophenyl)-1-piperazinecarboxylate

【CA登记号】

【分子式】C₁₆H₂₃N₃O₅

【分子量】337.37584

【元素组成】C 56.96% H 6.87% N 12.46% O 23.71%

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)

Nitration of 1-(2-methoxyphenyl)piperazine (I) using KNO3 in H2SO4 gave (II). After protection of (II) as the N-Boc derivative (III), reduction of the nitro group by catalytic hydrogenation over Pd/C yielded aniline (IV). This was condensed with 5-chloro-3-methylbenzothiophene-2-sulfonyl chloride (V) to afford the corresponding sulfonamide (VI). Finally, the Boc protecting group of (VI) was removed with HCl in boiling THF.

参考文献中间体

合成目标

【1】 Bromidge, S.M.; Brown, A.M.; Clarke, S.E.; Dodgson, K.; Gager, T.; Grassam, H.L.; Jeffrey, P.M.; Joiner, G.F.; King, F.D.; Middlemiss, D.N.; Moss, S.F.; Newman, H.; Riley, G.; Routledge, C.; Wyman, P.; 5-Chloro-N-(4-methoxy-3-piperazin-1-ylphenyl)-3-methyl-2-benzothiophenesulfonamide (SB-271046): A potent, selective, and orally bioavailable 5-HT6 receptor antagonist. J Med Chem 1999, 42, 2, 202.
【2】 King, F.D.; Bromidge, S.M.; Wyman, P.A. (SmithKline Beecham plc); Sulphonamide derivs., process for their preparation, and their use as medicaments. WO 9827081 .

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)	11882	1-(2-Methoxyphenyl)piperazine; Methyl 2-piperazinophenyl ether; 1-(2-Methoxyphenyl)-piperazine	35386-24-4	C₁₁H₁₆N₂O	详情	详情
(II)	25384	1-(2-methoxy-5-nitrophenyl)piperazine		C₁₁H₁₅N₃O₃	详情	详情
(III)	25385	tert-butyl 4-(2-methoxy-5-nitrophenyl)-1-piperazinecarboxylate		C₁₆H₂₃N₃O₅	详情	详情
(IV)	25386	tert-butyl 4-(5-amino-2-methoxyphenyl)-1-piperazinecarboxylate		C₁₆H₂₅N₃O₃	详情	详情
(V)	25387	5-chloro-3-methyl-1-benzothiophene-2-sulfonyl chloride		C₉H₆Cl₂O₂S₂	详情	详情
(VI)	25388	tert-butyl 4-(5-[[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]amino]-2-methoxyphenyl)-1-piperazinecarboxylate		C₂₅H₃₀ClN₃O₅S₂	详情	详情

Extended Information