公开(公告)号：US10544121B2

公开(公告)日：2020-01-28

申请号：US16045896

申请日：2018-07-26

申请人： Dow AgroSciences LLC

发明人： Jason S. Fisk ,  Xiaoyong Li ,  Mark Muehlfeld ,  Robert S. Bauman ,  Jossian Oppenheimer ,  Siyu Tu ,  Mark A. Nitz ,  Reetam Chakrabarti ,  Shawn D. Feist ,  James W. Ringer ,  Ronald B. Leng

IPC分类号： C07D401/04 ,  B01J31/00 ,  B01J35/00 ,  C07D213/79 ,  C07D213/90 ,  C07D239/02 ,  C07D239/28 ,  C07D239/32

摘要： Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalkyl and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This includes synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.

公开(公告)号：US20180334444A1

公开(公告)日：2018-11-22

申请号：US16045896

申请日：2018-07-26

申请人： Dow AgroSciences LLC

发明人： Jason S. Fisk ,  Xiaoyong Li ,  Mark Muehlfeld ,  Robert S. Bauman ,  Jooossian Oppenheimer ,  Siyu Tu ,  Mark A. Nitz ,  Reetam Chakrabarti ,  Shawn D. Feist ,  James W. Ringer ,  Ronald B. Leng

IPC分类号： C07D401/04 ,  B01J31/00 ,  C07D213/79 ,  B01J35/00 ,  C07D239/02 ,  C07D239/28 ,  C07D239/32 ,  C07D213/90

CPC分类号： C07D401/04 ,  B01J31/00 ,  B01J31/04 ,  B01J35/0046 ,  B01J2231/4211 ,  B01J2531/824 ,  C07D213/79 ,  C07D213/90 ,  C07D239/02 ,  C07D239/28 ,  C07D239/32

摘要： Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalkyl and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This includes synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.

公开(公告)号：US10087164B2

公开(公告)日：2018-10-02

申请号：US15599716

申请日：2017-05-19

申请人： Dow AgroSciences LLC

发明人： Jason S. Fisk ,  Xiaoyong Li ,  Mark Muehlfeld ,  Robert S. Bauman ,  Jossian Oppenheimer ,  Siyu Tu ,  Mark A. Nitz ,  Reetam Chakrabarti ,  Shawn D. Feist ,  James W. Ringer ,  Ronald B. Leng

IPC分类号： C07D213/90 ,  C07D401/04 ,  C07D239/28 ,  B01J35/00 ,  C07D213/79 ,  C07D239/02 ,  C07D239/32

摘要： Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalkyl and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This invention was expanded to include synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.

公开(公告)号：US20170334878A1

公开(公告)日：2017-11-23

申请号：US15599716

申请日：2017-05-19

申请人： Dow AgroSciences LLC

发明人： Jason S. Fisk ,  Xiaoyong Li ,  Mark Muehlfeld ,  Robert S. Bauman ,  Jossian Oppenheimer ,  Siyu Tu ,  Mark A. Nitz ,  Reetam Chakrabarti ,  Shawn D. Feist ,  James W. Ringer ,  Ronald B. Leng

IPC分类号： C07D401/04 ,  C07D239/28 ,  C07D213/90 ,  B01J35/00 ,  C07D213/79 ,  C07D239/32 ,  C07D239/02

CPC分类号： C07D401/04 ,  B01J31/00 ,  B01J35/0046 ,  B01J2231/4211 ,  C07D213/79 ,  C07D213/90 ,  C07D239/02 ,  C07D239/28 ,  C07D239/32

摘要： Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalky and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This invention was expanded to include synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.

公开(公告)号：US10570114B2

公开(公告)日：2020-02-25

申请号：US16045901

申请日：2018-07-26

申请人： Dow AgroSciences LLC

发明人： Jason S. Fisk ,  Xiaoyong Li ,  Mark Muehlfeld ,  Robert S. Bauman ,  Jossian Oppenheimer ,  Siyu Tu ,  Mark A. Nitz ,  Reetam Chakrabarti ,  Shawn D. Feist ,  James W. Ringer ,  Ronald B. Leng

IPC分类号： C07D401/04 ,  C07D213/79 ,  C07D213/90 ,  C07D239/02 ,  C07D239/28 ,  C07D239/32 ,  B01J31/00 ,  B01J35/00

摘要： Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalkyl and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This includes synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.

公开(公告)号：US20180334445A1

公开(公告)日：2018-11-22

申请号：US16045901

申请日：2018-07-26

申请人： Dow AgroSciences LLC

发明人： Jason S. F ,  Xiaoyong Li ,  Mark Muehlfeld ,  Robert S. Bauman ,  Jossian Oppenheimer ,  Siyu Tu ,  Mark A. Nitz ,  Reetam Chakrabarti ,  Shawn D. Feist ,  James W. Ringer ,  Ronald B. Leng

IPC分类号： C07D401/04 ,  B01J31/00 ,  C07D213/79 ,  B01J35/00 ,  C07D239/02 ,  C07D239/28 ,  C07D239/32 ,  C07D213/90

CPC分类号： C07D401/04 ,  B01J31/00 ,  B01J31/04 ,  B01J35/0046 ,  B01J2231/4211 ,  B01J2531/824 ,  C07D213/79 ,  C07D213/90 ,  C07D239/02 ,  C07D239/28 ,  C07D239/32

摘要： Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalkyl and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This includes synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.