|
【结 构 式】 
|
【分子编号】26765 【品名】tert-butyl 3-[[1-(4-fluorobenzyl)-1H-benzimidazol-2-yl](methyl)amino]propyl(methyl)carbamate 【CA登记号】 |
【 分 子 式 】C24H31FN4O2 【 分 子 量 】426.5343032 【元素组成】C 67.58% H 7.33% F 4.45% N 13.14% O 7.5% |
合成路线1
该中间体在本合成路线中的序号：(VI)The reaction of 2-chlorobenzimidazole (I) with N,N'-dimethylprolylene-1,3-diamine (II) by heating at 130 C gives N-(1H-benzimidazol-2-yl)-N,N'-dimethylpropylene-1,3-diamine (III), which is treated with tert-butoxycarbonyl anhydride yielding the carbamate (IV). The condensation of (IV) with 4-fluorobenzyl chloride (V) by means of K2CO3 in DMF affords N-(benzyloxycarbonyl)-N'-[1-(4-fluorobenzyl)benzimidazol-2-yl)-N,N'-dimethylpropylene-1,3-diamine (VI), which is deprotected with trifluoroacetic acid providing the secondary amine (VII). Finally, this compound is condensed with phenyl N-[3,5-bis(trifluoromethyl)benzyl]carbamate (VIII) by heating at 120 C.
| 【1】 Kamikawaji, Y.; Tanikawa, K.; Yamamoto, A.; Hirotsuka, M.; Iwama, T.; Fujita, Y. (Nissan Chemical Industry, Ltd.); Benzimidazole deriv.. EP 0980359; JP 1999315071; US 6114369; WO 9850368 . |
| 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) | 26761 | 2-chloroimidazo[1,2-a]pyridine; 2-chlorobenzimidazole; 2-Amino-4'-chlorodiphenylether; 2-Aminodiphenylether; 2-chloro-1H-benzimidazole | 4857-06-1 | C7H5ClN2 | 详情 | 详情 |
| (II) | 26762 | N-methyl-N-[3-(methylamino)propyl]amine | 111-33-1 | C5H14N2 | 详情 | 详情 |
| (III) | 26763 | N(1)-(1H-benzimidazol-2-yl)-N(1),N(3)-dimethyl-1,3-propanediamine | C12H18N4 | 详情 | 详情 | |
| (IV) | 26764 | tert-butyl 3-[1H-benzimidazol-2-yl(methyl)amino]propyl(methyl)carbamate | C17H26N4O2 | 详情 | 详情 | |
| (V) | 12354 | 4-Fluorobenzyl chloride; 1-(Chloromethyl)-4-fluorobenzene | 352-11-4 | C7H6ClF | 详情 | 详情 |
| (VI) | 26765 | tert-butyl 3-[[1-(4-fluorobenzyl)-1H-benzimidazol-2-yl](methyl)amino]propyl(methyl)carbamate | C24H31FN4O2 | 详情 | 详情 | |
| (VII) | 26766 | N-[1-(4-fluorobenzyl)-1H-benzimidazol-2-yl]-N-methyl-N-[3-(methylamino)propyl]amine | C19H23FN4 | 详情 | 详情 | |
| (VIII) | 26767 | phenyl 3,5-bis(trifluoromethyl)benzylcarbamate | C16H11F6NO2 | 详情 | 详情 |