Parallel Synthesis of 1-Substituted 5-(5-Oxopyrrolidin-3-yl)-1H-pyrazole-4-carboxamides

被引：7

作者：

Perdih, Peter ^{[1
]}

Baskovc, Jernej ^{[1
]}

Dahmann, Georg ^{[2
]}

Groselj, Uros ^{[1
]}

Kocar, Drago ^{[1
]}

Novak, Ana ^{[1
]}

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, Med Chem, D-88397 Biberach, Germany

来源：

SYNTHESIS-STUTTGART | 2011年 / 17期

关键词：

pyrrolidinone; pyrazole; cyclocondensations; amidations; histamine analogues; SOLUTION-PHASE SYNTHESIS; AMIDE BOND FORMATION; COMPREHENSIVE SURVEY; VERSATILE SYNTHONS; CHEMICAL LIBRARIES; DRUG DISCOVERY; EFFICIENT; DERIVATIVES; RECEPTOR; HISTAMINE;

D O I：

10.1055/s-0030-1261034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A parallel solution-phase synthesis of 5-(5-oxo-1-phenylpyrrolidin- 3-yl)-1H-pyrazole-4-carboxamide derivatives as conformationally constrained pyrazole analogues of histamine starting from itaconic acid was developed. The synthetic method comprises a five-step preparation of 1-substituted 5-(5-oxo-1-phenylpyrrolidin- 3-yl)-1H-pyrazole-4-carboxylic acids followed by parallel amidation with various primary and secondary amines to give a library of 24 histamine analogues in good overall yields and in very high purities. The method is general and substrate-independent. All the amidations proceed smoothly and no major difference in reactivity is observed with respect to the structures of the reactants.

引用

页码：2822 / 2832

页数：11

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