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【结 构 式】 
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【分子编号】61936 【品名】1-(1-azidoethyl)-3-nitrobenzene 【CA登记号】 |
【 分 子 式 】C8H8N4O2 【 分 子 量 】192.17728 【元素组成】C 50% H 4.2% N 29.15% O 16.65% |
合成路线1
该中间体在本合成路线中的序号：(VIII)The reduction of 3-nitroacetophenone (VI) by means of NaBH4 in ethanol gives 1-(3-nitrophenyl)ethanol (VII), which is treated with DPPA and DBU in hot toluene to yield the azido derivative (VIII). The reduction of (VIII) with PPh3 in THF/water affords 1-(3-nitrophenyl)ethylamine (IX) as a racemic mixture that is submitted to optical resolution with L-(+)-tartaric acid to provide the desired (S)-isomer (X). The reduction of the nitro group of (X) by means of H2 over Pd/C in methanol gives 1(S)-(3-aminophenyl)ethylamine (XI), which is condensed with 2(R)-hydroxypentanenitrile (XII) and CDI to yield the carbamate (XIII). Finally, this compound is condensed with intermediate carbamate (V) by means of TEA in hot ethyl acetate to afford the target urea.
| 【1】 Saunders, J.; Bethiel, S.; Badia, M.; Stamos, D.; Trudeau, M. (Vertex Pharmaceuticals Inc.); Inhibitors of IMPDH enzyme. WO 0056331 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 61933 | phenyl 4-cyano-3-methoxyphenylcarbamate | C15H12N2O3 | 详情 | 详情 | |
| (VI) | 61934 | 1-(3-nitrophenyl)-1-ethanone；3-Nitroacetophenone;m-Nitroacetophenone | 121-89-1 | C8H7NO3 | 详情 | 详情 |
| (VII) | 61935 | 1-(3-nitrophenyl)-1-ethanol | C8H9NO3 | 详情 | 详情 | |
| (VIII) | 61936 | 1-(1-azidoethyl)-3-nitrobenzene | C8H8N4O2 | 详情 | 详情 | |
| (IX) | 61937 | 1-(3-nitrophenyl)ethylamine; 1-(3-nitrophenyl)-1-ethanamine | C8H10N2O2 | 详情 | 详情 | |
| (X) | 61938 | (1S)-1-(3-nitrophenyl)-1-ethanamine; (1S)-1-(3-nitrophenyl)ethylamine | C8H10N2O2 | 详情 | 详情 | |
| (XI) | 61939 | 3-[(1S)-1-aminoethyl]aniline; 3-[(1S)-1-aminoethyl]phenylamine | C8H12N2 | 详情 | 详情 | |
| (XII) | 61940 | (3R)-3-hydroxypentanenitrile | C5H9NO | 详情 | 详情 | |
| (XIII) | 61941 | (1R)-1-(cyanomethyl)propyl (1S)-1-(3-aminophenyl)ethylcarbamate | C14H19N3O2 | 详情 | 详情 |