【结 构 式】 |
【分子编号】49114 【品名】1H-benzimidazol-2-ylmethylamine; 1H-benzimidazol-2-ylmethanamine 【CA登记号】 |
【 分 子 式 】C8H9N3 【 分 子 量 】147.17968 【元素组成】C 65.29% H 6.16% N 28.55% |
合成路线1
该中间体在本合成路线中的序号:(VI)The title compound was prepared by solid-phase synthesis using a 2-chlorotrityl resin, chloride form. N2-(Benzyloxycarbonyl)-L-2,3-diaminopropionic acid (I) was protected as the Fmoc derivative (II) upon treatment with N-(Fmoc-oxy)succinimide. After attachment of the protected diaminoacid (II) to the chloride resin, the Fmoc group was selectively removed by means of piperidine in DMF to give the resin-bound Cbz-2,3-diaminopropionic acid (III). Acylation of the free amino function of (III) with 4-(chloromethyl)benzoyl chloride (IV) provided amide (V). The chloride group of (V) was then displaced with 2-(aminomethyl)benzimidazole (VI), yielding resin (VII). The required urea functionality (IX) was obtained by coupling (VII) with cyclohexyl isocyanate (VIII). Finally, cleavage of the carboxylic acid from the resin (IX) was achieved by treatment with trifluoroacetic acid in moist dichloromethane.
【1】 Neustadt, B.R.; Smith, E.M. (Schering Corp.); Benzimidazole cpds. that are vitronectin receptor antagonists. EP 1135374; WO 0032578 . |
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),(III) | 18008 | (2S)-3-amino-2-[[(benzyloxy)carbonyl]amino]propionic acid; N(alpha)-Z-L-2,3-diaminopropionic acid | 35761-26-3 | C11H14N2O4 | 详情 | 详情 |
(II) | 49111 | (2S)-2-[[(benzyloxy)carbonyl]amino]-3-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propionic acid | C26H24N2O6 | 详情 | 详情 | |
(IV) | 49112 | 4-(Chloromethyl)benzoyl chloride; p-(Chloromethyl)benzoyl chloride | 876-08-4 | C8H6Cl2O | 详情 | 详情 |
(V) | 49113 | (2S)-2-[[(benzyloxy)carbonyl]amino]-3-[[4-(chloromethyl)benzoyl]amino]propionic acid | C19H19ClN2O5 | 详情 | 详情 | |
(VI) | 49114 | 1H-benzimidazol-2-ylmethylamine; 1H-benzimidazol-2-ylmethanamine | C8H9N3 | 详情 | 详情 | |
(VII) | 49115 | (2S)-3-[(4-[[(1H-benzimidazol-2-ylmethyl)amino]methyl]benzoyl)amino]-2-[[(benzyloxy)carbonyl]amino]propionic acid | C27H27N5O5 | 详情 | 详情 | |
(VIII) | 10108 | N-Methyl(1-naphthyl)methanamine; N-Methyl-N-(1-naphthylmethyl)amine; 1-Methyl-1-naphthalenemethylamine | 65473-13-4 | C12H13N | 详情 | 详情 |
(IX) | 49116 | (2S)-3-[[4-([(1H-benzimidazol-2-ylmethyl)[(cyclohexylamino)carbonyl]amino]methyl)benzoyl]amino]-2-[[(benzyloxy)carbonyl]amino]propionic acid | C34H38N6O6 | 详情 | 详情 |