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【结 构 式】

【药物名称】L-750355

【化学名称】N-[4-[2-[3-(6-Aminopyridin-3-yloxy)-2(S)-hydroxypropylamino]ethyl]phenyl]-4-isopropylbenzenesulfonamide

【CA登记号】159183-92-3, 172902-22-6 (undefined isomer)

【 分 子 式 】C25H32N4O4S

【 分 子 量 】484.62219

【开发单位】Merck & Co. (Originator)

【药理作用】Antiobesity Drugs, METABOLIC DRUGS, Treatment of Nutritional Disorders, beta3-Adrenoceptor Agonists

合成路线1

The reaction of 2-acetamido-5-hydroxypyridine (I) with (S)-glycidol 3-nitrobenzenesulfonate (II) by means of NaOH in DMF gives 2(S)-(6-acetamido-3-pyridyloxymethyl)oxirane (III), which is condensed with 2-(4-nitrophenyl)ethylamine (IV) by means of triethylamine in refluxing methanol yielding the chiral isopropanol (V). The protection of the secondary amino group of (V) with tert-butoxycarbonyl anhydride affords the carbamate (VI), which is submitted to reduction at the nitro group with H2 over Pd/C in ethyl acetate providing the aniline derivative (VII). The acylation of (VII) with 4-iodobenzenesulfonyl chloride (VIII) and pyridine in dichloromethane affords the sulfonamide (IX), which is finally deprotected with 2N HCl in refluxing methanol.

1 Fisher, M.H.; Mathvink, R.J.; Ok, H.O.; Parmee, E.R.; Weber, A.E. (Merck & Co., Inc.); Substd. phenyl sulfonamides as selective beta3 agonists for the treatment of diabetes and obesity. CA 2114712; EP 0611003; JP 1995010827; US 5451677; WO 9418161 .
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) 27813 N-(5-hydroxy-2-pyridinyl)acetamide C7H8N2O2 详情 详情
(II) 16259 (2S)oxiranylmethyl 3-nitrobenzenesulfonate; (S)-(+)-Glycidyl nosylate 115314-14-2 C9H9NO6S 详情 详情
(III) 27814 N-[5-[(2S)oxiranylmethoxy]-2-pyridinyl]acetamide C10H12N2O3 详情 详情
(IV) 26560 4-nitrophenethylamine 24954-67-4 C8H10N2O2 详情 详情
(V) 27815 N-[5-([(2S)-2-hydroxy-3-[(4-nitrophenethyl)amino]propyl]oxy)-2-pyridinyl]acetamide C18H22N4O5 详情 详情
(VI) 27816 tert-butyl (2S)-3-[[6-(acetamido)-3-pyridinyl]oxy]-2-hydroxypropyl(4-nitrophenethyl)carbamate C23H30N4O7 详情 详情
(VII) 27817 tert-butyl (2S)-3-[[6-(acetamido)-3-pyridinyl]oxy]-2-hydroxypropyl(4-aminophenethyl)carbamate C23H32N4O5 详情 详情
(VIII) 28870 4-isopropylbenzenesulfonyl chloride 54997-90-9 C9H11ClO2S 详情 详情
(IX) 27818 tert-butyl (2S)-3-[[6-(acetamido)-3-pyridinyl]oxy]-2-hydroxypropyl(4-[[(4-isopropylphenyl)sulfonyl]amino]phenethyl)carbamate C32H42N4O7S 详情 详情
Extended Information