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【结 构 式】 
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【分子编号】40528 【品名】tert-butyl 4-(4-piperidinylamino)benzoate 【CA登记号】 |
【 分 子 式 】C16H24N2O2 【 分 子 量 】276.37884 【元素组成】C 69.53% H 8.75% N 10.14% O 11.58% |
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：(IV)Palladium-catalyzed coupling of 4-amino-1-benzylpiperidine (I) with tert-butyl 4-bromobenzoate (II) afforded the anilinopiperidine derivative (III). Removal of the benzyl protecting group of (III) to give (IV) was achieved by transfer hydrogenolysis in the presence of ammonium formate and Pd/C. Piperidine (IV) was then coupled with 4-amino-2-chloro-6,7-dimethoxyquinazoline (V) in hot isoamyl alcohol yielding piperidino quinazoline (VI). The title carboxylic acid was finally obtained by acidic deprotection of tert-butyl ester of (VI).
| 【1】 Casper, M.D.; Kung, P.-P.; Cook, K.L.; et al.; Structure-activity relationships of novel 2-substituted quinazoline antibacterial agents. J Med Chem 1999, 42, 22, 4705. |
| 【2】 Guinosso, C.J.; Cook, P.D.; Kung, P.-P. (Isis Pharmaceuticals, Inc.); Antibacterial quinazoline cpds.. US 6156758 . |
| 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) | 34808 | 1-Benzyl-4-piperidinylamine; 1-Benzyl-4-piperidinamine; 4-Amino-1-benzylpiperidine | 50541-93-0 | C12H18N2 | 详情 | 详情 |
| (II) | 14286 | tert-butyl 4-bromobenzoate | C11H13BrO2 | 详情 | 详情 | |
| (III) | 40527 | tert-butyl 4-[(1-benzyl-4-piperidinyl)amino]benzoate | C23H30N2O2 | 详情 | 详情 | |
| (IV) | 40528 | tert-butyl 4-(4-piperidinylamino)benzoate | C16H24N2O2 | 详情 | 详情 | |
| (V) | 10443 | 2-Chloro-6,7-dimethoxy-4-quinazolinamine; 4-Amino-2-chloro-6,7-dimethoxyquinazoline; 2-Chloro-6,7-dimethoxy-4-quinazolinylamine | 23680-84-4 | C10H10ClN3O2 | 详情 | 详情 |
| (VI) | 40529 | tert-butyl 4-[[1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-piperidinyl]amino]benzoate | C26H33N5O4 | 详情 | 详情 |
Extended Information