4-[(3-aminophenyl)(hydroxy)methyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide -Drug Synthesis Database

【结构式】

【分子编号】44146

【品名】4-[(3-aminophenyl)(hydroxy)methyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide

【CA登记号】

【分子式】C₁₂H₁₆N₄O₃S

【分子量】296.3502

【元素组成】C 48.64% H 5.44% N 18.91% O 16.2% S 10.82%

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)

Treatment of 4-iodo-N,N-dimethyl-1H-imidazole-1-sulfonamide (I) with EtMgBr and 3-nitrobenzaldehyde (II) in CH2Cl2 yields derivative (III), whose nitro moiety is reduced by hydrogenation over Pd/C in EtOAc to afford aminophenyl derivative (IV). Treatment of (IV) with Et3SiH in TFA provides aminobenzyl derivative (V), which is finally converted into the desired compound by treatment with pyridine and ethanesulfonyl chloride (VI) followed by reflux in HCl.

参考文献中间体

合成目标

【1】 Altenbach, R.J.; Holladay, M.W.; Carroll, W.A.; Meyer, M.D.; Kerwin, J.F. Jr.; Kolasa, T.; Rohde, J.; Khilevich, A. (Abbott Laboratories Inc.); Imidazoles and related cpds. as alpha1A agonists. WO 0007997 .

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)	44143	4-iodo-N,N-dimethyl-1H-imidazole-1-sulfonamide		C₅H₈IN₃O₂S	详情	详情
(II)	12646	3-Nitrobenzaldehyde	99-61-6	C₇H₅NO₃	详情	详情
(III)	44145	4-[hydroxy(3-nitrophenyl)methyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide		C₁₂H₁₄N₄O₅S	详情	详情
(IV)	44146	4-[(3-aminophenyl)(hydroxy)methyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide		C₁₂H₁₆N₄O₃S	详情	详情
(V)	44147	4-(3-aminobenzyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide		C₁₂H₁₆N₄O₂S	详情	详情
(VI)	54065	Ethanesulfonyl chloride; Ethylsulfonyl chloride	594-44-5	C₂H₅ClO₂S	详情	详情

Extended Information