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【结 构 式】 
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【分子编号】28167 【品名】2-cyano-3-(1-methyl-1H-pyrrol-2-yl)-3-oxo-N-phenylpropanamide 【CA登记号】 |
【 分 子 式 】C15H13N3O2 【 分 子 量 】267.28724 【元素组成】C 67.41% H 4.9% N 15.72% O 11.97% |
合成路线1
该中间体在本合成路线中的序号：(V)The esterification of N-methylpyrrol-2-carboxylic acid (I) with NaH and methyl iodide in DMF gives methyl N methylpyrrol 2 carboxylate (II), which is condensed with acetonitrile by means of NaH in DMF yielding 3-(1-methyl-2-pyrrolyl)-3-oxopropionitrile (III). The reaction of (III) with phenylisocyanate (IV) by means of triethylamine in toluene affords 2-cyano-3-(1-methyl-2-pyrrolyl)-3-oxo-N-phenylpropionamide (V), which is finally treated with triethanolamine (VI) in hot ethanol.
| 【1】 Walker, G.N. (Novartis AG); alpha-Carbamoyl-pyrrolpropionitriles, process fortheir preparation and pharmaceutical preparations containing them. EP 0143142 . |
| 【2】 Serradell, M.N.; Castaner, J.; Castaner, R.M.; Prinomide Triethanolamine. Drugs Fut 1987, 12, 8, 773. |
| 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) | 11286 | 1-Methyl-1H-pyrrole-2-carboxylic acid; 1-Methyl-2-pyrrolecarboxylic acid | 6973-60-0 | C6H7NO2 | 详情 | 详情 |
| (II) | 11287 | methyl 1-methyl-1H-pyrrole-2-carboxylate | 37619-24-2 | C7H9NO2 | 详情 | 详情 |
| (III) | 11288 | 3-(1-Methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile | C8H8N2O | 详情 | 详情 | |
| (IV) | 11289 | 1-Isocyanatobenzene; phenyl isocyanate; Phenylisocyanate | 103-71-9 | C7H5NO | 详情 | 详情 |
| (V) | 28167 | 2-cyano-3-(1-methyl-1H-pyrrol-2-yl)-3-oxo-N-phenylpropanamide | C15H13N3O2 | 详情 | 详情 | |
| (VI) | 28168 | 2-[bis(2-hydroxyethyl)amino]-1-ethanol | 102-71-6 | C6H15NO3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)The reaction of acid (I) with SOCl2 in ethyl ether containing triethylamine gives the corresponding acyl chloride (VII), which is condensed with ethyl cyanacetate (VIII) by means of NaH in glyme yielding ethyl 2-cyano-3-(1-methyl-2-pyrrolyl)-3-oxopropanoate (IX). The reaction of (IX) with aniline (X) in refluxing xylene affords the corresponding anilide (V) already obtained.
| 【1】 Walker, G.N. (Novartis AG); alpha-Carbamoyl-pyrrolpropionitriles, process fortheir preparation and pharmaceutical preparations containing them. EP 0143142 . |
| 【2】 Serradell, M.N.; Castaner, J.; Castaner, R.M.; Prinomide Triethanolamine. Drugs Fut 1987, 12, 8, 773. |
| 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) | 11286 | 1-Methyl-1H-pyrrole-2-carboxylic acid; 1-Methyl-2-pyrrolecarboxylic acid | 6973-60-0 | C6H7NO2 | 详情 | 详情 |
| (V) | 28167 | 2-cyano-3-(1-methyl-1H-pyrrol-2-yl)-3-oxo-N-phenylpropanamide | C15H13N3O2 | 详情 | 详情 | |
| (VI) | 28168 | 2-[bis(2-hydroxyethyl)amino]-1-ethanol | 102-71-6 | C6H15NO3 | 详情 | 详情 |
| (VII) | 28169 | 1-methyl-1H-pyrrole-2-carbonyl chloride | C6H6ClNO | 详情 | 详情 | |
| (VIII) | 11877 | Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate | 105-56-6 | C5H7NO2 | 详情 | 详情 |
| (IX) | 28170 | ethyl 2-cyano-3-(1-methyl-1H-pyrrol-2-yl)-3-oxopropanoate | C11H12N2O3 | 详情 | 详情 | |
| (X) | 12294 | Aniline; Phenylamine | 62-53-3 | C6H7N | 详情 | 详情 |