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【结 构 式】 
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【分子编号】55969 【品名】diethyl (2S)-2-({[5-(2-{2-[(2,2-dimethylpropanoyl)amino]-4-oxo-3,4,5,6,7,8-hexahydropyrido[2,3-d]pyrimidin-6-yl}ethyl)-4-methyl-2-thienyl]carbonyl}amino)pentanedioate 【CA登记号】 |
【 分 子 式 】C29H41N5O7S 【 分 子 量 】603.74004 【元素组成】C 57.69% H 6.84% N 11.6% O 18.55% S 5.31% |
合成路线1
该中间体在本合成路线中的序号：(VI)Acylation of diethyl L-glutamate (I) with 5-bromo-4-methylthiophene-2-carboxylic acid (II) using EDC as the coupling reagent provided amide (III). Subsequent palladium-catalyzed coupling between bromothiophene (III) and ethynyl pyridopyrimidinone (IV) furnished the disubstituted acetylene (V), which was further hydrogenated to (VI) in the presence of Pd/C in trifluoroacetic acid. Finally, basic hydrolysis of the ethyl ester and pivaloyl groups of (VI) led to the title compound.
| 【1】 Varney, M.D.; Romines, W.H. (Agouron Pharmaceuticals, Inc.); Cpds. useful as antiproliferative agents and GARFT inhibitors. WO 9603406 . |
| 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) | 11013 | diethyl (2S)-2-aminopentanedioate | C9H17NO4 | 详情 | 详情 | |
| (II) | 55966 | 5-bromo-4-methyl-2-thiophenecarboxylic acid | C6H5BrO2S | 详情 | 详情 | |
| (III) | 55967 | diethyl (2S)-2-{[(5-bromo-4-methyl-2-thienyl)carbonyl]amino}pentanedioate | C15H20BrNO5S | 详情 | 详情 | |
| (IV) | 14282 | N-(6-Ethynyl-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidin-2-yl)-2,2-dimethylpropanamide | C14H14N4O2 | 详情 | 详情 | |
| (V) | 55968 | diethyl (2S)-2-({[5-(2-{2-[(2,2-dimethylpropanoyl)amino]-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidin-6-yl}ethynyl)-4-methyl-2-thienyl]carbonyl}amino)pentanedioate | C29H33N5O7S | 详情 | 详情 | |
| (VI) | 55969 | diethyl (2S)-2-({[5-(2-{2-[(2,2-dimethylpropanoyl)amino]-4-oxo-3,4,5,6,7,8-hexahydropyrido[2,3-d]pyrimidin-6-yl}ethyl)-4-methyl-2-thienyl]carbonyl}amino)pentanedioate | C29H41N5O7S | 详情 | 详情 |