- Access to 2-pyridinylamide and imidazopyridine from 2-fluoropyridine and amidine hydrochloride
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Under catalyst-free conditions, an efficient method to synthesize 2-pyridinylamides has been developed, and the protocol uses inexpensive and readily available 2-fluoropyridine and amidine derivatives as the starting materials. Simultaneously, the copper-catalysed approach to imidazopyridine derivatives has been established with high chemoselectivity and regiospecificity. The results suggest that the nitrogen-heterocycles containing iodide substituents can also be compatible for the reaction via the cascade Ullmann-type coupling, and the nucleophilic substitution reaction provides the target products in a one-pot manner.
- Chen, Lu,Huang, Shuo,Ji, Xiaoliang,Li, Jiaming,Li, Jian,Li, Yibiao,Liu, Jiasheng,Peng, Shiyong,Zhang, Kun
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supporting information
p. 9292 - 9299
(2020/12/03)
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- Preparation of the HIV Attachment Inhibitor BMS-663068. Part 1. Evolution of Enabling Strategies
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The development of two enabling routes that led to the production of >1000 kg of BMS-663068 (3) is described. The route identified for the initial 100 kg delivery to support development activities and initial clinical trials involved the conversion of 2-amino-4-picoline to the parent active pharmaceutical ingredient (API), followed by pro-drug installation and deprotection. To eliminate the problematic isolation of the parent API and synthesis of di-t-butyl(chloromethyl)phosphate, a second-generation pro-drug installation route was developed which involved the conversion of a late-stage common intermediate to an N(1)-thioether derivative followed by chloromethylation, displacement with di-t-butylpotassium phosphate, and deprotection. This second strategy resulted in the multikilogram scale preparation of the API in 14 linear steps and ~7% overall yield.
- Fox, Richard J.,Tripp, Jonathan C.,Schultz, Mitchell J.,Payack, Joseph F.,Fanfair, Dayne D.,Mudryk, Boguslaw M.,Murugesan, Saravanababu,Chen, Chung-Pin H.,La Cruz, Thomas E.,Ivy, Sabrina E.,Broxer, Sévrine,Cullen, Ryan,Erdemir, Deniz,Geng, Peng,Xu, Zhongmin,Fritz, Alan,Doubleday, Wendel W.,Conlon, David A.
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p. 1095 - 1109
(2017/08/23)
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- METHODS OF MAKING HIV ATTACHMENT INHIBITOR PRODRUG COMPOUND AND INTERMEDIATES
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A method for making the compound of Formula ( I ) is set forth using alkylation, amidation, chlorination and phosphate installation procedures.
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Page/Page column 13
(2012/08/27)
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- SUBSTITUTED IMIDAZOQUINOLINE DERIVATIVES AS KINASE INHIBITORS
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The present invention relates to substituted imidazo[4,5-c]quinoline derivatives, the compounds of formula (I), wherein R1 R2, R3, R4, R5, R6 and R7 are as defined in the specification, processes for their preparation, pharmaceutical compositions comprising compounds of formula (I), and their use in the treatment of diseases or disorders mediated by one or more kinases, particularly proliferative diseases or disorders such as cancer. These compounds can also be used in the treatment of inflammatory diseases and angiogenesis related disorders.
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Page/Page column 79
(2012/02/02)
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- PYRIDYLAMIDINE COMPOUND OR SALT THEREOF, AND AGRICULTURAL OR HORTICULTURAL FUNGICIDE COMPOSITION CONTAINING THE SAME AS ACTIVE INGREDIENT
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An agricultural or horticultural fungicide composition having stabilized high plant disease control effect is provided. The agricultural or horticultural fungicide composition contains a pyridylamidine compound represented by the formula (I): or a salt th
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Page/Page column 15
(2009/09/04)
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- Method of producing 2-acyl amino 5-halogenopyridine compounds
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A 2-amino-3-nitro-5-halogenopyridine is formed from a 2-acylaminopyridine by way of a 2-acylamino-5-halogenopyridine. The 2-acetamido-5-bromopyridine may be formed from the 2-acylaminopyridine by way of a 2-acylaminopyridinium-HBr3 salt.
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- Method of producing 2-amino-3-nitro-5-halogenopyridine
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A 2-amino-3-nitro-5-halogenopyridine is formed from a 2-acylaminopyridine by way of a 2-acylamino-5-halogenopyridine. The 2-acetamido-5-bromopyridine may be formed from the 2-acylaminopyridine by way of a 2-acylaminopyridinium-HBr3 salt.
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