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【结 构 式】 
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【分子编号】43957 【品名】tert-butyl (5S,6R,7R)-7-[2-[3-(acetoxy)-2-methylpropyl]-4-methoxyphenyl]-5-(2,2-difluoro-1,3-benzodioxol-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate 【CA登记号】 |
【 分 子 式 】C33H35F2NO7 【 分 子 量 】595.6402464 【元素组成】C 66.54% H 5.92% F 6.38% N 2.35% O 18.8% |
合成路线1
该中间体在本合成路线中的序号：(XIII)Resolution of (XII) by chiral HPLC and then acetylation of the hydroxyl group gave the chiral acetate (XIII). The pyridine ring of (XIII) was converted to the corresponding N-oxide (XIV) by means of meta-chloroperbenzoic acid. Subsequent displacement of the N-oxide of (XIV) with N-isopropyl-benzimidoyl chloride (XV) introduced the N-benzoyl-N-isopropylamino group into the pyridine to afford (XVI). After tert-butyl ester cleavage with trifluoroacetic acid, yielding (XVIII), basic hydrolysis of the benzamido group provided the title compound.
| 【1】 Hayama, T.; Ohtake, N.; Niiyama, K.; et al.; New cyclopentenopyridine derivatives. A potent, orally active, selective endothelin ETA receptor antagonist. 16th Int Symp Med Chem (Sept 18 2000, Bologna) 2000, Abst PA-78. |
| 【2】 Nishikibe, M.; Hayama, T.; Otake, N. (Banyu Pharmaceutical Co., Ltd.); Substd. 5-(2,2-difluoro-1,3-benzodioxol-5-yl) cyclopentenopyridine deriv.. EP 1049691; WO 9937639 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XII) | 43955 | tert-butyl (5S,6R,7R)-5-(2,2-difluoro-1,3-benzodioxol-5-yl)-7-[2-(3-hydroxy-2-methylpropyl)-4-methoxyphenyl]-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate | C31H33F2NO6 | 详情 | 详情 | |
| (XIII) | 43957 | tert-butyl (5S,6R,7R)-7-[2-[3-(acetoxy)-2-methylpropyl]-4-methoxyphenyl]-5-(2,2-difluoro-1,3-benzodioxol-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate | C33H35F2NO7 | 详情 | 详情 | |
| (XIV) | 43958 | (5S,6R,7R)-7-[2-[3-(acetoxy)-2-methylpropyl]-4-methoxyphenyl]-6-(tert-butoxycarbonyl)-5-(2,2-difluoro-1,3-benzodioxol-5-yl)-6,7-dihydro-5H-cyclopenta[b]pyridinium-1-olate | C33H35F2NO8 | 详情 | 详情 | |
| (XV) | 43959 | N-isopropylbenzenecarboximidoyl chloride | C10H12ClN | 详情 | 详情 | |
| (XVI) | 43960 | tert-butyl (5S,6R,7R)-2-[benzoyl(isopropyl)amino]-5-(2,2-difluoro-1,3-benzodioxol-5-yl)-7-[2-(3-hydroxy-2-methylpropyl)-4-methoxyphenyl]-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate | C41H44F2N2O7 | 详情 | 详情 | |
| (XVII) | 43961 | (5S,6R,7R)-2-[benzoyl(isopropyl)amino]-5-(2,2-difluoro-1,3-benzodioxol-5-yl)-7-[2-(3-hydroxy-2-methylpropyl)-4-methoxyphenyl]-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylic acid | C37H36F2N2O7 | 详情 | 详情 |