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【结 构 式】

【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%

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:(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
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