Synthesis of p38 MAP kinase inhibitor BIRB 796 and analogs via copper-mediated N-arylation reaction

被引：1

作者：

Tan, Zhulin ^{[1
]}

Song, Jinhua J. ^{[1
]}

Reeves, Jonathan T. ^{[1
]}

Fandrick, Daniel R. ^{[1
]}

Lee, Heewon ^{[1
]}

Campbell, Scot ^{[1
]}

Yee, Nathan K. ^{[1
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, Ridgefield, CT 06877 USA

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 34期

关键词：

ARYLBORONIC ACID; UREAS; AMINES;

D O I：

10.1016/j.tetlet.2010.06.109

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct N-arylation of urea (5) with various arylboronic acids mediated by cupric acetate furnished BIR8796 and a range of N-substituted BIRB796 analogs in good to moderate yields in one step. Urea (5) was readily synthesized from commercially available compounds. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：4547 / 4551

页数：5

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[1] Synthesis and biological evaluation of BIRB 796 analogs as potent inhibitors of p38 MAP kinase.
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