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【结 构 式】 
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【分子编号】64003 【品名】tert-butyl 4-{propyl[5-(trifluoromethyl)-2-pyrimidinyl]amino}-1-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C18H27F3N4O2 【 分 子 量 】388.4333496 【元素组成】C 55.66% H 7.01% F 14.67% N 14.42% O 8.24% |
合成路线1
该中间体在本合成路线中的序号：(XXVIII)Reductive amination of N-Boc-4-piperidone (XXII) with benzylamine, followed by benzyl group hydrogenolysis of the resultant secondary amine (XXIII) gives rise to N-Boc-4-aminopiperidine (XXIV). This is then condensed with 2-chloro-5-trifluoromethylpyrimidine (XXV) to furnish adduct (XXVI). Subsequent alkylation of amine (XXVI) with allyl bromide in the presence of sodium hexamethyldisilazide affords the N-allyl amine (XXVII), which is further hydrogenated to the N-propyl analogue (XXVIII). Acidic hydrolysis of (XXVIII) then removes the N-Boc protecting group, providing piperidine (XXIX). (1,2)
| 【1】 1,3,4 Trisubstituted pyrrolidine CCR5 receptor antagonists bearing 4-aminoheterocycle substituted piperidine side chains. Bioorg Med Chem Lett 2003, 13, 3, 427. |
| 【2】 Mills, S.G.; Kim, D.; Hale, J.; MacCoss, M.; Berk, S.; Chapman, K.; Lynch, C.; Caldwell, C.; Willoughby, C.; Kim, R.M. (Merck & Co., Inc.); Pyrrolidine modulators of chemokine receptor activity. US 6498161; WO 0059498 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXII) | 18620 | tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone | 79099-07-3 | C10H17NO3 | 详情 | 详情 |
| (XXIII) | 63999 | tert-butyl 4-(benzylamino)-1-piperidinecarboxylate | C17H26N2O2 | 详情 | 详情 | |
| (XXIV) | 28914 | benzyl 4-ethyl-3,4,6,7-tetrahydro-5H-imidazo[4,5-c]pyridine-5-carboxylate | C16H19N3O2 | 详情 | 详情 | |
| (XXV) | 64000 | 2-chloro-5-(trifluoromethyl)pyrimidine | C5H2ClF3N2 | 详情 | 详情 | |
| (XXVI) | 64001 | tert-butyl 4-{[5-(trifluoromethyl)-2-pyrimidinyl]amino}-1-piperidinecarboxylate | C15H21F3N4O2 | 详情 | 详情 | |
| (XXVII) | 64002 | tert-butyl 4-{allyl[5-(trifluoromethyl)-2-pyrimidinyl]amino}-1-piperidinecarboxylate | C18H25F3N4O2 | 详情 | 详情 | |
| (XXVIII) | 64003 | tert-butyl 4-{propyl[5-(trifluoromethyl)-2-pyrimidinyl]amino}-1-piperidinecarboxylate | C18H27F3N4O2 | 详情 | 详情 | |
| (XXIX) | 64004 | N-(4-piperidinyl)-N-propyl-5-(trifluoromethyl)-2-pyrimidinamine; N-(4-piperidinyl)-N-propyl-N-[5-(trifluoromethyl)-2-pyrimidinyl]amine | C13H19F3N4 | 详情 | 详情 |