- Synthesis of Pyridinyl-Pyrimidines via Pd-Catalyzed Cross-Coupling Reactions: A Comparison of Classical Thermal and Microwave Assisted Reaction Conditions
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The Negishi cross-coupling reaction was used for the synthesis of pyridinyl-pyrimidines utilizing classical thermal or microwave assisted conditions. The organozinc substrates were prepared from 2-fluoro-4-iodopyridine by conventional lithiation chemistry and subsequent transmetalation with ZnCl2 or ZnI2. Two different catalysts - Pd(PPh3)4 and Pd/C - were investigated for their ability to facilitate the cross coupling process with 2,4-dichloropyrimidine. We found that distribution and yield of desired compounds and possible by-products highly depend on the type of energy input. In contrast to thermal conditions, the microwave assisted method allowed efficient access to di-coupled compounds.
- Stanetty, Peter,Schnürch, Michael,Mihovilovic, Marko D.
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- SERINE/THREONINE KINASE INHIBITORS
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Compounds of Formula I or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof are provided, which are useful for the treatment of diseases. Methods of using compounds of Formula I or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such diseases, or associated pathological conditions are disclosed.
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- Discovery of highly potent, selective, and efficacious small molecule inhibitors of ERK1/2
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Using structure-based design, a novel series of pyridone ERK1/2 inhibitors was developed. Optimization led to the identification of (S)-14k, a potent, selective, and orally bioavailable agent that inhibited tumor growth in mouse xenograft models. On the basis of its in vivo efficacy and preliminary safety profiles, (S)-14k was selected for further preclinical evaluation.
- Ren, Li,Grina, Jonas,Moreno, David,Blake, James F.,Gaudino, John J.,Garrey, Rustam,Metcalf, Andrew T.,Burkard, Michael,Martinson, Matthew,Rasor, Kevin,Chen, Huifen,Dean, Brian,Gould, Stephen E.,Pacheco, Patricia,Shahidi-Latham, Sheerin,Yin, Jianping,West, Kristina,Wang, Weiru,Moffat, John G.,Schwarz, Jacob B.
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p. 1976 - 1991
(2015/04/27)
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- SERINE/THREONINE KINASE INHIBITORS
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Compounds of Formula I or a stereoisomer, tautomer, prodrug or pharmaceutically acceptable salt thereof are provided, which are useful for the treatment of hyperproliferative, pain and inflammatory diseases. Methods of using compounds of Formula I or a stereoisomer, tautomer, prodrug or pharmaceutically acceptable salt thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.
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Paragraph 00262
(2013/09/12)
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- Discovery of the macrocycle (9 E)-15-(2-(Pyrrolidin-1-yl)ethoxy)-7,12,25- trioxa-19,21,24-triaza-tetracyclo[18.3.1.1(2,5).1(14,18)]hexacosa-1(24),2,4,9, 14(26),15,17,20,22-nonaene (SB1578), a potent inhibitor of Janus kinase 2/Fms-liketyrosine kinase-3 (J
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Herein, we describe the synthesis and SAR of a series of small molecule macrocycles that selectively inhibit JAK2 kinase within the JAK family and FLT3 kinase. Following a multiparameter optimization of a key aryl ring of the previously described SB1518 (
- William, Anthony D.,Lee, Angeline C.-H.,Poulsen, Anders,Goh, Kee Chuan,Madan, Babita,Hart, Stefan,Tan, Evelyn,Wang, Haishan,Nagaraj, Harish,Chen, Dizhong,Lee, Chai Ping,Sun, Eric T.,Jayaraman, Ramesh,Pasha, Mohammad Khalid,Ethirajulu, Kantharaj,Wood, Jeanette M.,Dymock, Brian W.
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experimental part
p. 2623 - 2640
(2012/06/01)
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- PYRIDYL SUBSTITUTED PYRIMIDINE DERIVATIVES
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The present invention relates to pyridyl substituted pyrimidine compounds that are useful as agents for the treatment of kinase related disorders such as proliferative disorders. More particularly, the present invention relates to oxygen linked and pyridy
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Page/Page column 59
(2009/01/20)
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- Novel and efficient access to phenylamino-pyrimidine type protein kinase C inhibitors utilizing a Negishi cross-coupling strategy
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A novel, short, and efficient synthetic pathway to 3-{4-[2-(3- chlorophenylamino)-pyrimidin-4-yl]-pyridin-2-ylamino}-propanol (CGP 60474) and a series of analogues was developed. The synthetic sequence consisted of a Negishi-type cross-coupling reaction i
- Stanetty, Peter,Hattinger, Gregor,Schnuerch, Michael,Mihovilovic, Marko D.
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p. 5215 - 5220
(2007/10/03)
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