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870604-65-2

870604-65-2

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Relevant articles and documentsAll total 1 Articles be found

RAF MODULATORS AND METHODS OF USE

-

, (2010/02/14)

The present invention relates to compounds of the Formula I, wherein G, A, X1, X2, X3, Z, E, Y, and X are defined herein. The compounds modulate protein kinase enzymatic activity to modulate cellular activities such as proliferation, differentiation, programmed cell death, migration and chemoinvasion. Compounds of the invention inhibit, regulate and/or modulate kinases, particularly Raf. Methods of using and preparing the compounds, and pharmaceutical compositions thereof, to treat kinase-dependent diseases and conditions are also an aspect of the invention.

Process route upstream and downstream products

Process route

phenylmethyl 2-{[3-nitro-4-({2-oxo-2-[(phenylmethyl)oxy]ethyl}amino)phenyl]carbonyl}benzoate

phenylmethyl 2-{[3-nitro-4-({2-oxo-2-[(phenylmethyl)oxy]ethyl}amino)phenyl]carbonyl}benzoate

2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid
870604-65-2

2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid

Conditions
Conditions Yield
With hydrogen; palladium 10% on activated carbon; In tetrahydrofuran; ethyl acetate; under 2068.65 Torr;
2-(4'-chloro-3'-nitrobenzoyl)benzoic acid
85-54-1

2-(4'-chloro-3'-nitrobenzoyl)benzoic acid

2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid
870604-65-2

2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: potassium hydroxide; water / 15 h / 90 °C
1.2: pH ~ 5
2.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C
3.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran; ethyl acetate / 2068.65 Torr
With potassium hydroxide; water; hydrogen; potassium carbonate; palladium 10% on activated carbon; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;
2-({4-[(carboxymethyl)amino]-3-nitrophenyl}carbonyl)benzoic acid

2-({4-[(carboxymethyl)amino]-3-nitrophenyl}carbonyl)benzoic acid

2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid
870604-65-2

2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C
2: hydrogen / palladium 10% on activated carbon / tetrahydrofuran; ethyl acetate / 2068.65 Torr
With hydrogen; potassium carbonate; palladium 10% on activated carbon; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;
2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid
870604-65-2

2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid

3-chloro-aniline
108-42-9

3-chloro-aniline

7-[2-(3-chlorophenyl)-1-hydroxy-3-oxo-2,3-dihydro-1H isoindol-1-yl]-3,4-dihydroquinoxalin-2(1H)-one

7-[2-(3-chlorophenyl)-1-hydroxy-3-oxo-2,3-dihydro-1H isoindol-1-yl]-3,4-dihydroquinoxalin-2(1H)-one

Conditions
Conditions Yield
2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid; With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; HATU; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h;
3-chloro-aniline; In N,N-dimethyl-formamide; at 20 ℃; for 15h;
39%
2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid
870604-65-2

2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

methyl 2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoate

methyl 2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoate

Conditions
Conditions Yield
2-[(3-oxo-1,2,3,4-tetrahydroquinoxalin-6-yl)carbonyl]benzoic acid; diazomethyl-trimethyl-silane; In methanol; hexane; benzene;
With acetic acid; In methanol; hexane; benzene;

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