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【结 构 式】

【分子编号】18747

【品名】4-(4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile

【CA登记号】

【 分 子 式 】C13H10F3N3O2

【 分 子 量 】297.2366296

【元素组成】C 52.53% H 3.39% F 19.18% N 14.14% O 10.77%

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:(V)

The reaction of 4-cyano-3-(trifluoromethyl)aniline (I) with phosgene afforded isocyanate (II). Subsequent condensation with 2-amino-2-methylpropionitrile (III) in the presence of Et3N in dichloroethane yielded the iminoimidazolidinone (IV), which was hydrolyzed to hydantoin (V) with refluxing 0.5 M HCl. Finally, alkylation with bromoacetonitrile (VI) in the presence of NaH in DMF provided the cyanomethyl compound.

1 Battmann, T.; et al.; Pharmacological profile of RU 58642, a potent systemic antiandrogen for the treatment of androgen-dependent disorders. J Steroid Biochem Mol Biol 1998, 64, 1-2, 103.
2 Gaillard-Kelly, M.; Goubet, F.; Philibert, D.; Teutsch, J.-G. (Aventis Pharma SA); Phenylimidazolidines, their process for fabrication, their application as medicaments and the pharmaceutical compsns. containing them. EP 0494819; FR 2671348; JP 1992308579; US 5411981 .
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) 18743 4-amino-2-(trifluoromethyl)benzonitrile;5-Amino-2-cyanobenzotrifluoride 654-70-6 C8H5F3N2 详情 详情
(II) 18744 4-isocyanato-2-(trifluoromethyl)benzonitrile C9H3F3N2O 详情 详情
(III) 18745 2-amino-2-methylpropanenitrile 19355-69-2 C4H8N2 详情 详情
(IV) 18746 4-(5-imino-4,4-dimethyl-2-oxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile C13H11F3N4O 详情 详情
(V) 18747 4-(4,4-dimethyl-2,5-dioxo-1-imidazolidinyl)-2-(trifluoromethyl)benzonitrile C13H10F3N3O2 详情 详情
(VI) 31883 2-bromoacetonitrile 590-17-0 C2H2BrN 详情 详情
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