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【结 构 式】 
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【分子编号】61663 【品名】1-[(4-{2-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylamino)carbonyl]hydrazino}-3-nitrophenyl)sulfonyl]-1H-pyrrole-2-carboxylic acid 【CA登记号】 |
【 分 子 式 】C27H23N5O7S 【 分 子 量 】561.57512 【元素组成】C 57.75% H 4.13% N 12.47% O 19.94% S 5.71% |
合成路线1
该中间体在本合成路线中的序号：(XII)Sulfonylation of pyrrole-2-carboxylic acid (VII) with 4-chloro-3-nitrobenzenesulfonyl chloride (VIII) in the presence of butyllithium leads to sulfonamide (IX). Chloride displacement in (IX) with hydrazine hydrate in refluxing THF affords the phenylhydrazine derivative (X). This is further coupled with isocyanate (XI) to produce the semicarbazide (XII). Finally, condensation of carboxylic acid (XII) with amine (VI), via activation as the mixed anhydride with isopropyl chloroformate, yields the title pyrrolecarboxamide.
| 【1】 Dziadulewicz, E.K.; et al.; Nonpeptide bradykinin B2 receptor antagonists: Conversion of rodent-selective bradyzide analogues into potent, orally-active human bradykinin B2 receptor antagonists. J Med Chem 2002, 45, 11, 2160. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 61664 | N~1~-(2-aminoethyl)-N~1~,N~3~,N~3~-trimethyl-1,3-propanediamine | C8H21N3 | 详情 | 详情 | |
| (VII) | 31796 | Pyrrole-2-carboxylic acid; 1H-pyrrole-2-carboxylic acid | 634-97-9 | C5H5NO2 | 详情 | 详情 |
| (VIII) | 42318 | 4-chloro-3-nitrobenzenesulfonyl chloride | 97-08-5 | C6H3Cl2NO4S | 详情 | 详情 |
| (IX) | 61660 | 1-[(4-chloro-3-nitrophenyl)sulfonyl]-1H-pyrrole-2-carboxylic acid | C11H7ClN2O6S | 详情 | 详情 | |
| (X) | 61661 | 1-[(4-hydrazino-3-nitrophenyl)sulfonyl]-1H-pyrrole-2-carboxylic acid | C11H10N4O6S | 详情 | 详情 | |
| (XI) | 61662 | 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl isocyanate; 5-isocyanato-10,11-dihydro-5H-dibenzo[a,d]cycloheptene | C16H13NO | 详情 | 详情 | |
| (XII) | 61663 | 1-[(4-{2-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylamino)carbonyl]hydrazino}-3-nitrophenyl)sulfonyl]-1H-pyrrole-2-carboxylic acid | C27H23N5O7S | 详情 | 详情 |