Synthesis of a naphthyridone p38 MAP kinase inhibitor

…, RJ Cvetovich, M McLaughlin, J Amato…

Index: Chung, John Y. L.; Cvetovich, Raymond J.; McLaughlin, Mark; Amato, Joseph; Tsay, Fuh-Rong; Jensen, Mark; Weissman, Steve; Zewge, Daniel Journal of Organic Chemistry, 2006 , vol. 71, # 22 p. 8602 - 8609

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Citation Number: 19

Abstract

Compound 1 is a p38 MAP kinase inhibitor potentially useful for the treatment of rheumatoid arthritis and psoriasis. A novel six-step synthesis suitable for large-scale preparation was developed in support of a drug development program at Merck Research Laboratories. The key steps include a tandem Heck-lactamization, N-oxidation, and a highly chemoselective Grignard addition of 4-(N-tert-butylpiperidinyl) magnesium chloride to a naphthyridone N- ...

 Related Synthetic Route
Piperidinium,1,1-dimethyl-4-oxo-, iodide (1:1) Structure

26822-37-7

Piperidinium,1,...

tert-Butylamine Structure

75-64-9

tert-Butylamine

~86%

1-tert-Butylpiperidin-4-one Structure

1465-76-5

1-tert-Butylpip...

N-Methyl-4-piperidone Structure

1445-73-4

N-Methyl-4-pipe...

~%

1-Tert-Butyl-4-chloropiperidine Structure

5570-81-0

1-Tert-Butyl-4-...

1-tert-Butylpiperidin-4-one Structure

1465-76-5

1-tert-Butylpip...

~%

1-Tert-Butyl-4-chloropiperidine Structure

5570-81-0

1-Tert-Butyl-4-...

Piperidinium,1,1-dimethyl-4-oxo-, iodide (1:1) Structure

26822-37-7

Piperidinium,1,...

~%

1-Tert-Butyl-4-chloropiperidine Structure

5570-81-0

1-Tert-Butyl-4-...

2-Chloro-4-bromopyridine Structure

73583-37-6

2-Chloro-4-brom...

~79%

4-Bromo-2-chloro-3-iodopyridine Structure

916203-52-6

4-Bromo-2-chlor...

4-Amino-2-chloropyridine Structure

14432-12-3

4-Amino-2-chlor...

~95%

2-Chloro-4-bromopyridine Structure

73583-37-6

2-Chloro-4-brom...

N-Methyl-4-piperidone Structure

1445-73-4

N-Methyl-4-pipe...

methyl iodide Structure

74-88-4

methyl iodide

~99%

Piperidinium,1,1-dimethyl-4-oxo-, iodide (1:1) Structure

26822-37-7

Piperidinium,1,...

4-Bromo-2-chloro-3-iodopyridine Structure

916203-52-6

4-Bromo-2-chlor...

N-(2,6-dichlorophenyl)prop-2-enamide Structure

37511-45-8

N-(2,6-dichloro...

~81%

5-Chloro-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one Structure

916203-59-3

5-Chloro-1-(2,6...

2-Chloro-4-bromopyridine Structure

73583-37-6

2-Chloro-4-brom...

~%

5-Chloro-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one Structure

916203-59-3

5-Chloro-1-(2,6...

4-Amino-2-chloropyridine Structure

14432-12-3

4-Amino-2-chlor...

~%

5-Chloro-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one Structure

916203-59-3

5-Chloro-1-(2,6...

N/A Structure

913556-82-8

N/A

~85%

7-chloro-1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2-one Structure

872973-93-8

7-chloro-1-(2,6...

4-Bromo-2-chloro-3-iodopyridine Structure

916203-52-6

4-Bromo-2-chlor...

~%

7-chloro-1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2-one Structure

872973-93-8

7-chloro-1-(2,6...

5-Chloro-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one Structure

916203-59-3

5-Chloro-1-(2,6...

~%

7-chloro-1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2-one Structure

872973-93-8

7-chloro-1-(2,6...

2-Chloro-4-bromopyridine Structure

73583-37-6

2-Chloro-4-brom...

~%

7-chloro-1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2-one Structure

872973-93-8

7-chloro-1-(2,6...

4-Amino-2-chloropyridine Structure

14432-12-3

4-Amino-2-chlor...

~%

7-chloro-1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2-one Structure

872973-93-8

7-chloro-1-(2,6...

N-(2,6-dichlorophenyl)prop-2-enamide Structure

37511-45-8

N-(2,6-dichloro...

~%

7-chloro-1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2-one Structure

872973-93-8

7-chloro-1-(2,6...

1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2(1H)-one Structure

444665-44-5

1-(2,6-dichloro...

~%

7-chloro-1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-1,6-naphthyridin-2-one Structure

872973-93-8

7-chloro-1-(2,6...


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