• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】64204

【品名】ethyl 2-[3-{[(1S)-2-azido-1-benzylethyl]amino}-2-oxo-1(2H)-pyrazinyl]acetate

【CA登记号】

【 分 子 式 】C17H20N6O3

【 分 子 量 】356.38444

【元素组成】C 57.29% H 5.66% N 23.58% O 13.47%

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:(XI)

Mitsunobu coupling of N-Boc-L-phenylglycinol (VIII) with hydrazoic acid affords azide (IX). Subsequent acidic cleavage of the N-Boc protecting group of (IX) furnishes amino azide (X). This is then condensed with the bromopyrazinone (VII) upon heating at 110 C in a pressure vessel to furnish adduct (XI). Treatment of (XI) with N-chlorosuccinimide in hot dichloroethane gives rise to the chloropyrazinone (XII). The azido group of (XII) is then reduced to the corresponding amine (XIII) employing SnCl2 in MeOH/THF (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
(VII) 63219 ethyl 2-[3-bromo-2-oxo-1(2H)-pyrazinyl]acetate C8H9BrN2O3 详情 详情
(VIII) 54624 tert-butyl (1S)-1-benzyl-2-hydroxyethylcarbamate C14H21NO3 详情 详情
(IX) 63851 tert-butyl (1S)-2-azido-1-benzylethylcarbamate C14H20N4O2 详情 详情
(X) 63852 (1S)-2-azido-1-benzylethylamine; (2S)-1-azido-3-phenyl-2-propanamine C9H12N4 详情 详情
(XI) 64204 ethyl 2-[3-{[(1S)-2-azido-1-benzylethyl]amino}-2-oxo-1(2H)-pyrazinyl]acetate C17H20N6O3 详情 详情
(XII) 64205 ethyl 2-[3-{[(1S)-2-azido-1-benzylethyl]amino}-6-chloro-2-oxo-1(2H)-pyrazinyl]acetate C17H19ClN6O3 详情 详情
(XIII) 64206 ethyl 2-[3-{[(1S)-2-amino-1-benzylethyl]amino}-6-chloro-2-oxo-1(2H)-pyrazinyl]acetate C17H21ClN4O3 详情 详情
Extended Information