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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information