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【结 构 式】

【分子编号】31347

【品名】3,4-difluoro-2-nitrophenylamine; 3,4-difluoro-2-nitroaniline

【CA登记号】

【 分 子 式 】C6H4F2N2O2

【 分 子 量 】174.1068464

【元素组成】C 41.39% H 2.32% F 21.82% N 16.09% O 18.38%

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:(I)

Addition of acrylonitrile (II) to 3,4-difluoro-2-nitroaniline (I) gave the anilinopropionitrile (III). Subsequent hydrogenation of the nitro group of (III) over Pd/C led to the phenylenediamine (IV), which was condensed with carbethoxyacetimidate-HCl (V) to produce the benzimidazole (VI). After conversion of the nitrile group of (VI) to ester (VII) with ethanolic HCl, Dieckmann condensation using NaOEt furnished the cyclic ketoester (VIII). Finally, reaction of (VIII) with 2,6-difluoroaniline (IX) in xylene yielded the target carboxamide.

1 Maryanoff, B.E.; et al.; Potential anxiolytic agents. Pyrido[1, 2-a]benzimidazoles: A new structural class of ligands for the benzodiazepine binding site on GABA-A receptors. J Med Chem 1995, 38, 1, 16.
2 Nortey, S.O.; Sanfilippo, P.J.; Dubinsky, B.; Maryanoff, B.E.; McComsey, D.F.; Reitz, A.B.; Shank, R.P.; McNally, J.J.; Potential anxiolytic agents. 3. Novel A-ring modified pyrido[1,2-a]benzimidazoles. Bioorg Med Chem Lett 1999, 9, 11, 1547.
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) 31347 3,4-difluoro-2-nitrophenylamine; 3,4-difluoro-2-nitroaniline C6H4F2N2O2 详情 详情
(II) 10847 Acrylonitrile 107-13-1 C3H3N 详情 详情
(III) 31348 3-(3,4-difluoro-2-nitroanilino)propanenitrile C9H7F2N3O2 详情 详情
(IV) 31349 3-(2-amino-3,4-difluoroanilino)propanenitrile C9H9F2N3 详情 详情
(V) 17929 ethyl 3-ethoxy-3-iminopropanoate 2318-25-4 C7H13NO3 详情 详情
(VI) 31350 ethyl 2-[1-(2-cyanoethyl)-4,5-difluoro-1H-benzimidazol-2-yl]acetate C14H13F2N3O2 详情 详情
(VII) 31351 ethyl 3-[2-(2-ethoxy-2-oxoethyl)-4,5-difluoro-1H-benzimidazol-1-yl]propanoate C16H18F2N2O4 详情 详情
(VIII) 31352 ethyl 6,7-difluoro-3-oxo-1,2,3,5-tetrahydropyrido[1,2-a]benzimidazole-4-carboxylate C14H12F2N2O3 详情 详情
(IX) 17933 2,6-Difluorophenylamine; 2,6-Difluoroaniline 5509-65-9 C6H5F2N 详情 详情
Extended Information