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【结 构 式】 
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【分子编号】45506 【品名】tert-butyl 4-[[(4-[[amino(imino)methyl]amino]benzyl)amino]carbonyl]-1-piperazinecarboxylate 【CA登记号】 |
【 分 子 式 】C18H28N6O3 【 分 子 量 】376.45896 【元素组成】C 57.43% H 7.5% N 22.32% O 12.75% |
合成路线1
该中间体在本合成路线中的序号：(VIII)4-Aminobenzylamine (I) was protected as the tert-butyl carbamate (II) upon treatment with Boc2O. Heating of (II) with cyanamide afforded guanidine (III). The Boc protecting group of (III) was then removed by means of trifluoroacetic acid to furnish 4-guanidinobenzylamine (IV). 4-Boc-piperazine-1-carbonyl chloride (VI) (obtained by treatment of N-Boc piperazine (V) with triphosgene) was condensed with amine (IV), yielding urea (VII). The N-Boc group of (VII) was then deprotected with trifluoroacetic acid to give (VIII) (1). Dianhydromannitol (X) was converted to bischloroformate (XI) by treatment with phosgene. Then condensation of (XI) with piperazine (VIII) provided the title biscarbamate.
| 【2】 Gangloff, A.R.; Kuo, E.Y.-L.; Dener, J.M.; Rice, K.D. (Axys Pharmaceuticals, Inc.); Compsns. and methods for treating mast-cell inflammatory condition. US 6022969; WO 9609297 . |
| 【1】 Putnam, D.; Dener, J.M.; Gangloff, A.R.; Wong, M.; Rice, K.D.; Wng, V.R.; Young, W.B.; Simpson, P.J.; Kuo, E.Y.-L.; Cregar, L.; Newcomb, W.S.; Dibasic inhibitors of human mast cell tryptase. Part 2: Structure-activity relationships and requirements for potent activity. Bioorg Med Chem Lett 2000, 10, 20, 2361. |
| 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) | 35548 | 4-(aminomethyl)aniline; 4-aminobenzylamine | 4403-71-8 | C7H10N2 | 详情 | 详情 |
| (II) | 35549 | tert-butyl 4-aminobenzylcarbamate | C12H18N2O2 | 详情 | 详情 | |
| (III) | 45504 | tert-butyl 4-[[amino(imino)methyl]amino]benzylcarbamate | C13H20N4O2 | 详情 | 详情 | |
| (IV) | 45505 | N-[4-(aminomethyl)phenyl]guanidine | C8H12N4 | 详情 | 详情 | |
| (V) | 13225 | N-tert-Butoxycarbonyl piperazine; tert-butyl 1-piperazinecarboxylate;tert-butyl piperazine-1-carboxylate | 143238-38-4 | C9H18N2O2 | 详情 | 详情 |
| (VI) | 28999 | tert-butyl 4-(chlorocarbonyl)-1-piperazinecarboxylate | C10H17ClN2O3 | 详情 | 详情 | |
| (VII) | 45507 | N-(4-[[amino(imino)methyl]amino]benzyl)-1-piperazinecarboxamide | C13H20N6O | 详情 | 详情 | |
| (VIII) | 45506 | tert-butyl 4-[[(4-[[amino(imino)methyl]amino]benzyl)amino]carbonyl]-1-piperazinecarboxylate | C18H28N6O3 | 详情 | 详情 | |
| (IX) | 45508 | (3R,3aR,6R,6aR)hexahydrofuro[3,2-b]furan-3,6-diol | 3261-62-9 | C6H10O4 | 详情 | 详情 |
| (X) | 45509 | (3R,3aS,6R,6aS)-3,6-bis[(chlorocarbonyl)oxy]hexahydrofuro[3,2-b]furan | 67-73-2 | C8H8Cl2O6 | 详情 | 详情 |