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【结 构 式】

【分子编号】32510

【品名】4-[1-(phenylsulfonyl)-1H-imidazol-4-yl]-3-butynyl 4-methylbenzenesulfonate

【CA登记号】

【 分 子 式 】C20H18N2O5S2

【 分 子 量 】430.5054

【元素组成】C 55.8% H 4.21% N 6.51% O 18.58% S 14.9%

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)

Coupling of 3-butyn-1-ol (I) with 4-iodo-1-phenylsulfonylimidazole (II) in the presence of CuI and Pd(PPh3)4 afforded the imidazolylbutynol (III), which was activated as the tosylate (IV) with p-toluenesulfonyl chloride in pyridine. Subsequent displacement of the tosylate group of (IV) by 4-benzylpiperidine (V) using NaHCO3 in hot DMF produced the corresponding N-(imidazolylbutynyl)piperidine with simultaneous cleavage of the benzenesulfonyl protecting group.

1 Serpa, K.A.; Wise, L.D.; Meltzer, L.T.; Gregory, T.F.; Wright, J.L.; Boxer, P.A.; Discovery of subtype-selective NMDA receptor ligands: 4-benzyl-1-piperidinylalkynylpyrroles, pyrazoles and imidazoles as NR1A/2B antagonists. Bioorg Med Chem Lett 1999, 9, 19, 2815.
2 Boxer, P.A.; Woodward, R.M.; Meltzer, L.T.; D'Wise, L.; Gregory, T.F.; Novel series of 4-benzyl-N-(4-imidazole-1-alkynyl)piperidines as potent subtype selective NMDA receptor antagonists. 218th ACS Natl Meet (Aug 22 1999, New Orleans) 1999, Abst MEDI 94.
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) 32507 3-butyn-1-ol 927-74-2 C4H6O 详情 详情
(II) 32508 4-iodo-1-(phenylsulfonyl)-1H-imidazole C9H7IN2O2S 详情 详情
(III) 32509 4-[1-(phenylsulfonyl)-1H-imidazol-4-yl]-3-butyn-1-ol C13H12N2O3S 详情 详情
(IV) 32510 4-[1-(phenylsulfonyl)-1H-imidazol-4-yl]-3-butynyl 4-methylbenzenesulfonate C20H18N2O5S2 详情 详情
(V) 26225 4-benzylpiperidine 31252-42-3 C12H17N 详情 详情
Extended Information