A synthesis of 1-substituted 5-[2-(acylamino)ethyl]-1H-pyrazole-4-carboxamides

被引：19

作者：

Kralj, David ^{[1
]}

Friedrich, Miha ^{[1
]}

Groselj, Uros ^{[1
]}

Kiraly-Potpara, Sonja ^{[1
]}

Meden, Anton ^{[1
]}

Wagger, Jernej ^{[1
]}

Dahmann, Georg ^{[2
]}

Stanovnik, Branko ^{[1
]}

Svete, Jurij ^{[1
]}

机构：

[1] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana 1000, Slovenia

[2] Boehringer Ingelheim Pharma GmbH & Co KG, Dept Chem Res, D-88397 Biberach, Germany

来源：

TETRAHEDRON | 2009年 / 65卷 / 34期

关键词：

Enaminones; Hydrazines; Pyrazoles; Carboxamides; Histamine analogues; COMBINATORIAL LIBRARY SYNTHESIS; SOLUTION-PHASE SYNTHESIS; COMPREHENSIVE SURVEY; AMINO-ACIDS; STEREOSELECTIVE CYCLOADDITIONS; PYRIDAZINE DERIVATIVES; COUPLING-CONSTANTS; CHEMICAL LIBRARIES; DRUG DISCOVERY; TRANSFORMATIONS;

D O I：

10.1016/j.tet.2009.06.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A seven-step synthesis of 1-substituted 5-(2-acylaminoethyl)-1H-pyi-azole-4-carboxamides 20 as the pyrazole analogues of histamine was developed. The synthesis starts with a three-step preparation of N(1)-substituted methyl 5-(2-tert-butoxycarbonylaminoethyl)-1H-pyrazole-4-carboxylates 7 from commercially available Boc-beta-alanine (1). Subsequent four-step transformation of the key-intermediates 7 into the final products 20 was performed following two complementary reaction sequences comprising acidolytic removal of the Boc group, hydrolysis of the COOMe group, amidations of the COOH group, and acylations of the NH2 group. The Structures of pyrazole derivatives were determined by spectroscopic methods and by X-ray diffraction. (C) 2009 Published by Elsevier Ltd.

引用

页码：7151 / 7162

页数：12

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