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【结 构 式】 
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【分子编号】64222 【品名】ethyl 2-[3-({(1S)-2-[(3-{[2-(aminomethyl)phenethyl]amino}propyl)amino]-1-benzylethyl}amino)-6-chloro-2-oxo-1(2H)-pyrazinyl]acetate 【CA登记号】 |
【 分 子 式 】C29H39ClN6O3 【 分 子 量 】555.12 【元素组成】C 62.75% H 7.08% Cl 6.39% N 15.14% O 8.65% |
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：(XXXI)Reductive condensation between aldehyde (XXV) and amine (XIII) in the presence of NaBH(OAc)3 leads to adduct (XXX). The N-Boc protecting groups of (XXX) are then cleaved under acidic conditions yielding tetra-amine (XXXI). Saponification of the ethyl ester group of (XXXI) with LiOH furnishes amino acid (XXXII). Finally, the title compound is obtained by macrocyclization of (XXXII) employing EDC/HOAt as the coupling reagent (1,2).
| 【1】 Nantermet, P.G.; Barrow, J.C.; Newton, C.L.; Pellicore, J.M.; Young, M.; Lewis, S.D.; Lucas, B.J.; Krueger, J.A.; McMasters, D.R.; Youwei, Y.; Kuo, L.C.; Vacca, J.P.; Selnick, H.G.; Design and synthesis of potent and selective macrocyclic thrombin inhibitors. 225th ACS Natl Meet (March 23 2003, New Orleans) 2003, Abst MEDI 168. |
| 【2】 Selnick, H.G.; Newton, R.C.; Newton, C.L.; Barrow, J.C.; Nantermet, P.G. (Merck & Co., Inc.); Thrombin inhibitors. WO 0311222 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIII) | 64206 | ethyl 2-[3-{[(1S)-2-amino-1-benzylethyl]amino}-6-chloro-2-oxo-1(2H)-pyrazinyl]acetate | C17H21ClN4O3 | 详情 | 详情 | |
| (XXV) | 64217 | tert-butyl 2-{[(tert-butoxycarbonyl)amino]methyl}phenethyl(3-oxopropyl)carbamate | C22H34N2O5 | 详情 | 详情 | |
| (XXX) | 64221 | ethyl 2-[3-{[(1S)-1-benzyl-2-({3-[(tert-butoxycarbonyl)(2-{[(tert-butoxycarbonyl)amino]methyl}phenethyl)amino]propyl}amino)ethyl]amino}-6-chloro-2-oxo-1(2H)-pyrazinyl]acetate | C39H55ClN6O7 | 详情 | 详情 | |
| (XXXI) | 64222 | ethyl 2-[3-({(1S)-2-[(3-{[2-(aminomethyl)phenethyl]amino}propyl)amino]-1-benzylethyl}amino)-6-chloro-2-oxo-1(2H)-pyrazinyl]acetate | C29H39ClN6O3 | 详情 | 详情 | |
| (XXXII) | 64223 | 2-[3-({(1S)-2-[(3-{[2-(aminomethyl)phenethyl]amino}propyl)amino]-1-benzylethyl}amino)-6-chloro-2-oxo-1(2H)-pyrazinyl]acetic acid | C27H35ClN6O3 | 详情 | 详情 |
Extended Information