Product Name

  • Name

    Regorafenib

  • EINECS 815-051-1
  • CAS No. 755037-03-7
  • Article Data30
  • CAS DataBase
  • Density 1.491 g/cm3
  • Solubility DMSO
  • Melting Point 206.0 to 210.0 °C
  • Formula C21H15ClF4N4O3
  • Boiling Point 513.4 °C at 760 mmHg
  • Molecular Weight 482.822
  • Flash Point 264.3 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 755037-03-7 (Regorafenib)
  • Hazard Symbols
  • Synonyms 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]-3-fluorophenoxy]-N-methylpyridine-2-carboxamide;4-(4-(3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido)-3-fluorophenoxy)-N-methylpicolinamide;
  • PSA 92.35000
  • LogP 6.22570

Synthetic route

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide
757251-39-1

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide

Methyl 4-methyl-3-oxopentanoate
42558-54-3

Methyl 4-methyl-3-oxopentanoate

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 140℃; for 4h; Temperature; Green chemistry;96.8%
...Expand
4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide
757251-39-1

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide

S,S-dimethyl dithiocarbonate
868-84-8

S,S-dimethyl dithiocarbonate

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide In tetrahydrofuran at 35℃; for 1.33333h; Green chemistry;96.2%
...Expand
4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide
757251-39-1

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide

4-chloro-3-(trifluoromethyl)phenyl isocyanate
327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 1.5h;94.5%
In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;90%
In dichloromethane for 24h;87%
4-amino-3-fluorophenol
399-95-1

4-amino-3-fluorophenol

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Reflux
2.1: 1-methyl-pyrrolidin-2-one / 100 °C
2.2: 4.17 h / 100 °C
2.3: 0.17 h / 80 °C
3.1: toluene; tetrahydrofuran / 4.5 h / 20 °C
3.2: 2.25 h
View Scheme
Multi-step reaction with 3 steps
1.1: cyclohexane / Reflux
2.1: 1-methyl-pyrrolidin-2-one / 100 °C
2.2: 3.67 h / 100 °C
2.3: 0.17 h / 80 °C
3.1: toluene; tetrahydrofuran / 4.5 h / 20 °C
3.2: 2.25 h
View Scheme
Multi-step reaction with 3 steps
1.1: Reflux
2.1: 1-methyl-pyrrolidin-2-one / 100 °C
2.2: 5.5 h / 100 °C
2.3: 0.17 h / 80 °C
3.1: toluene; tetrahydrofuran / 4.5 h / 20 °C
3.2: 2.25 h
View Scheme
Multi-step reaction with 2 steps
1.1: potassium tert-butylate / N,N-dimethyl acetamide / 0.42 h / 0 °C
1.2: 16 h / 100 °C
2.1: toluene / 72 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: dichloromethane / 6 h / Reflux
2: potassium tert-butylate; potassium carbonate / N,N-dimethyl-formamide / 3 h / 90 °C
View Scheme
C12H16FNO
1338722-52-3

C12H16FNO

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1-methyl-pyrrolidin-2-one / 100 °C
1.2: 4.17 h / 100 °C
1.3: 0.17 h / 80 °C
2.1: toluene; tetrahydrofuran / 4.5 h / 20 °C
2.2: 2.25 h
View Scheme
C11H14FNO
1338722-53-4

C11H14FNO

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1-methyl-pyrrolidin-2-one / 100 °C
1.2: 5.5 h / 100 °C
1.3: 0.17 h / 80 °C
2.1: toluene; tetrahydrofuran / 4.5 h / 20 °C
2.2: 2.25 h
View Scheme
3-fluoro-4-nitrophenol
394-41-2

3-fluoro-4-nitrophenol

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 4 h
2.1: potassium tert-butylate / N,N-dimethyl acetamide / 0.42 h / 0 °C
2.2: 16 h / 100 °C
3.1: toluene / 72 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / diethylene glycol dimethyl ether / 6 h / Reflux
2: hydrogen / methanol / 3 h / 20 °C / 1520.1 Torr / Autoclave
3: tetrahydrofuran / 5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere
2: hydrogen; 5%-palladium/activated carbon / ethyl acetate / 1125.11 Torr
3: dichloromethane / 3 h / 0 - 25 °C
View Scheme
2-Picolinic acid
98-98-6

2-Picolinic acid

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium bromide / chlorobenzene / 0.25 h / 50 °C
1.2: 23 h / 85 °C
2.1: water; toluene / 7 h / 20 °C
3.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.5 h / 20 °C
3.2: 5 h / 100 °C
4.1: sulfuric acid; nitric acid / water / 1.5 h / -10 - 0 °C
5.1: ammonium chloride; iron; hydrogenchloride / water; ethanol / 0.25 h / Reflux
6.1: ethyl acetate / 1.5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: thionyl chloride / N,N-dimethyl-formamide
2.1: sodium hydroxide / tetrahydrofuran / 3 h / -5 °C
3.1: potassium tert-butylate / dimethyl amine / 2 h / 20 °C / Inert atmosphere
3.2: 85 °C / Inert atmosphere
4.1: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: thionyl chloride; sodium bromide / N,N-dimethyl-formamide / 30 h / 80 °C
2.1: sodium hydroxide / tetrahydrofuran / 3 h / -5 °C
3.1: potassium tert-butylate / dimethyl amine / 2 h / 20 °C / Inert atmosphere
3.2: 85 °C / Inert atmosphere
4.1: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: N,N-dimethyl-formamide; thionyl chloride / 18 h / 70 °C / Inert atmosphere; Schlenk technique
2.1: tetrahydrofuran; methanol; water / 1 h / 0 - 10 °C / Inert atmosphere; Schlenk technique
3.1: potassium tert-butylate; potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique
3.2: 16 h / 110 °C / Inert atmosphere; Schlenk technique
4.1: sulfuric acid; nitric acid / water / 1 h / 0 °C / Inert atmosphere; Schlenk technique
4.2: 1 h / 80 °C / Inert atmosphere; Schlenk technique
5.1: dichloromethane; ethyl acetate / 18 h / 20 °C / Inert atmosphere; Schlenk technique
View Scheme
4-chloro-2-pyridine carboxylic acid chloride hydrochloride

4-chloro-2-pyridine carboxylic acid chloride hydrochloride

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: water; toluene / 7 h / 20 °C
2.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.5 h / 20 °C
2.2: 5 h / 100 °C
3.1: sulfuric acid; nitric acid / water / 1.5 h / -10 - 0 °C
4.1: ammonium chloride; iron; hydrogenchloride / water; ethanol / 0.25 h / Reflux
5.1: ethyl acetate / 1.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tetrahydrofuran / 16.42 h / 0 - 20 °C / Inert atmosphere
2.1: potassium tert-butylate / N,N-dimethyl-formamide / 3.03 h / Inert atmosphere
2.2: 10 h / 90 °C / Inert atmosphere
3.1: dichloromethane / 24 h
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / tetrahydrofuran / 3 h / -5 °C
2.1: potassium tert-butylate / dimethyl amine / 2 h / 20 °C / Inert atmosphere
2.2: 85 °C / Inert atmosphere
3.1: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: tetrahydrofuran; methanol; water / 1 h / 0 - 10 °C / Inert atmosphere; Schlenk technique
2.1: potassium tert-butylate; potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique
2.2: 16 h / 110 °C / Inert atmosphere; Schlenk technique
3.1: sulfuric acid; nitric acid / water / 1 h / 0 °C / Inert atmosphere; Schlenk technique
3.2: 1 h / 80 °C / Inert atmosphere; Schlenk technique
4.1: dichloromethane; ethyl acetate / 18 h / 20 °C / Inert atmosphere; Schlenk technique
View Scheme
4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium tert-butylate / N,N-dimethyl-formamide / 0.5 h / 20 °C
1.2: 5 h / 100 °C
2.1: sulfuric acid; nitric acid / water / 1.5 h / -10 - 0 °C
3.1: ammonium chloride; iron; hydrogenchloride / water; ethanol / 0.25 h / Reflux
4.1: ethyl acetate / 1.5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium hydroxide / N,N-dimethyl-formamide / 0.5 h / 0 - 50 °C
1.2: 100 °C
2.1: sulfuric acid; nitric acid / 1.5 h / -10 - 0 °C
3.1: iron; ammonium chloride; hydrogenchloride / water; ethanol / 1 h / Reflux
4.1: ethyl acetate / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium tert-butylate / N,N-dimethyl-formamide / 3.03 h / Inert atmosphere
1.2: 10 h / 90 °C / Inert atmosphere
2.1: dichloromethane / 24 h
View Scheme
4-(3-fluorophenoxy)-N-methylpyridine-2-carboxamide

4-(3-fluorophenoxy)-N-methylpyridine-2-carboxamide

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid; nitric acid / water / 1.5 h / -10 - 0 °C
2: ammonium chloride; iron; hydrogenchloride / water; ethanol / 0.25 h / Reflux
3: ethyl acetate / 1.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid; nitric acid / 1.5 h / -10 - 0 °C
2: iron; ammonium chloride; hydrogenchloride / water; ethanol / 1 h / Reflux
3: ethyl acetate / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sulfuric acid; nitric acid / water / 1 h / 0 °C / Inert atmosphere; Schlenk technique
1.2: 1 h / 80 °C / Inert atmosphere; Schlenk technique
2.1: dichloromethane; ethyl acetate / 18 h / 20 °C / Inert atmosphere; Schlenk technique
View Scheme
4-(4-nitro-3-fluorophenoxy)-N-methylpyridine-2-carboxamide

4-(4-nitro-3-fluorophenoxy)-N-methylpyridine-2-carboxamide

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium chloride; iron; hydrogenchloride / water; ethanol / 0.25 h / Reflux
2: ethyl acetate / 1.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: iron; ammonium chloride; hydrogenchloride / water; ethanol / 1 h / Reflux
2: ethyl acetate / 0.5 h / 20 °C
View Scheme
3-fluorophenol
372-20-3

3-fluorophenol

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium hydroxide / N,N-dimethyl-formamide / 0.5 h / 0 - 50 °C
1.2: 100 °C
2.1: sulfuric acid; nitric acid / 1.5 h / -10 - 0 °C
3.1: iron; ammonium chloride; hydrogenchloride / water; ethanol / 1 h / Reflux
4.1: ethyl acetate / 0.5 h / 20 °C
View Scheme
ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: oxalic acid; aluminium / water / 1.5 h / 80 - 85 °C
2: potassium tert-butylate / N,N-dimethyl acetamide / 1.5 h / 0 - 90 °C
3: tetrahydrofuran / 12 h / 30 °C
View Scheme
4-chloropicolinic acid
5470-22-4

4-chloropicolinic acid

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 15.5 h / 0 - 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 16.42 h / 0 - 20 °C / Inert atmosphere
3.1: potassium tert-butylate / N,N-dimethyl-formamide / 3.03 h / Inert atmosphere
3.2: 10 h / 90 °C / Inert atmosphere
4.1: dichloromethane / 24 h
View Scheme
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide
757251-39-1

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
With cetyltrimethylammonium hydroxide In dichloromethane at 35℃; for 1.33333h;21.99 g
...Expand
4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide
757251-39-1

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide

4-chloro-3-(trifluoromethyl)benzoic acid
1737-36-6

4-chloro-3-(trifluoromethyl)benzoic acid

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Stage #1: 4-chloro-3-(trifluoromethyl)benzoic acid With pyridine; diphenylphosphoranyl azide In 1,4-dioxane at 0℃; for 1.5h; Reflux;
Stage #2: 4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide In 1,4-dioxane for 1h; Reflux;
methyl 4-chloropyridine-2-carboxylate hydrochloride

methyl 4-chloropyridine-2-carboxylate hydrochloride

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanol / tetrahydrofuran
2.1: potassium tert-butylate / dimethyl amine / 2 h / 20 °C / Inert atmosphere
2.2: 85 °C / Inert atmosphere
3.1: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
View Scheme
N-(2-fluoro-4-hydroxyphenyl)acetamide
103842-00-8

N-(2-fluoro-4-hydroxyphenyl)acetamide

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride / water / 80 °C / Inert atmosphere
2.1: potassium tert-butylate / dimethyl amine / 2 h / 20 °C / Inert atmosphere
2.2: 85 °C / Inert atmosphere
3.1: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
View Scheme
4-amino-3-fluorophenol
399-95-1

4-amino-3-fluorophenol

4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium tert-butylate / dimethyl amine / 2 h / 20 °C / Inert atmosphere
1.2: 85 °C / Inert atmosphere
2.1: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
View Scheme
4-chloro-3-(trifluoromethyl)phenyl isocyanate
327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 6 h / Reflux
2: potassium tert-butylate; potassium carbonate / N,N-dimethyl-formamide / 3 h / 90 °C
View Scheme
3-chloro-N-methyl-benzamide
18370-10-0

3-chloro-N-methyl-benzamide

1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-4-hydroxyphenyl)urea
1333390-56-9

1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-4-hydroxyphenyl)urea

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
With potassium tert-butylate; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 3h;
C7H4FN3O2

C7H4FN3O2

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene; N,N-dimethyl-formamide / 90 °C / Inert atmosphere
2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h
2.2: 6 h / 80 °C
View Scheme
2-fluoro-4-hydroxybenzoic acid
65145-13-3

2-fluoro-4-hydroxybenzoic acid

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 0.08 h / 0 °C / Inert atmosphere
2.1: sodium azide; dmap / toluene; N,N-dimethyl-formamide / Inert atmosphere
3.1: toluene; N,N-dimethyl-formamide / 90 °C / Inert atmosphere
4.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h
4.2: 6 h / 80 °C
View Scheme
C19H14FO4P

C19H14FO4P

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium azide; dmap / toluene; N,N-dimethyl-formamide / Inert atmosphere
2.1: toluene; N,N-dimethyl-formamide / 90 °C / Inert atmosphere
3.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h
3.2: 6 h / 80 °C
View Scheme
1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-4-hydroxyphenyl)urea
1333390-56-9

1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-4-hydroxyphenyl)urea

4-chloro-N-methylpicolinamide
220000-87-3

4-chloro-N-methylpicolinamide

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Stage #1: 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-4-hydroxyphenyl)urea With potassium tert-butylate In N,N-dimethyl-formamide for 2h;
Stage #2: 4-chloro-N-methylpicolinamide With potassium carbonate at 80℃; for 6h;
1-chloro-2-(trifluoromethyl)benzene
88-16-4

1-chloro-2-(trifluoromethyl)benzene

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuric acid; nitric acid / water / 18 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
2: iron; ammonium chloride; hydrogenchloride / ethanol; water / 2 h / 80 °C / Inert atmosphere; Schlenk technique
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere; Schlenk technique
4: dichloromethane; ethyl acetate / 18 h / 20 °C / Inert atmosphere; Schlenk technique
View Scheme
4-chloro-3-(trifluoromethyl)nitrobenzene
777-37-7

4-chloro-3-(trifluoromethyl)nitrobenzene

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: iron; ammonium chloride; hydrogenchloride / ethanol; water / 2 h / 80 °C / Inert atmosphere; Schlenk technique
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere; Schlenk technique
3: dichloromethane; ethyl acetate / 18 h / 20 °C / Inert atmosphere; Schlenk technique
View Scheme
4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide
757251-39-1

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide

N-[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl chloride
348-91-4

N-[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl chloride

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide; acetonitrile at 15 - 30℃; for 1h; Large scale;24.17 kg
4-chloro-3-(trifluoromethyl)-N-(triphenylphosphanylidene)anilinium bromide

4-chloro-3-(trifluoromethyl)-N-(triphenylphosphanylidene)anilinium bromide

regorafenib
755037-03-7

regorafenib

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.17 h
1.2: 0.33 h / 20 °C
2.1: toluene
View Scheme
regorafenib
755037-03-7

regorafenib

cis-dichlorobis(dimethylsulfoxide)platinum(II)
75992-73-3, 25794-47-2, 30729-25-0, 15274-33-6, 22840-91-1, 14568-13-9

cis-dichlorobis(dimethylsulfoxide)platinum(II)

Pt(regorafenib)(DMSO)Cl2

Pt(regorafenib)(DMSO)Cl2

Conditions
ConditionsYield
In methanol; water at 55℃; for 36h; Temperature; Solvent; Autoclave;95%
In methanol; acetone at 65℃; for 24h;
regorafenib
755037-03-7

regorafenib

maleic acid
110-16-7

maleic acid

C21H15ClF4N4O3*C4H4O4

C21H15ClF4N4O3*C4H4O4

Conditions
ConditionsYield
In methanol; n-heptane at 20℃; for 4h; Solvent;90.7%
heptanedioic acid
111-16-0

heptanedioic acid

regorafenib
755037-03-7

regorafenib

C21H15ClF4N4O3*C7H12O4

C21H15ClF4N4O3*C7H12O4

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h; Solvent;89.4%
regorafenib
755037-03-7

regorafenib

malonic acid
141-82-2

malonic acid

C21H15ClF4N4O3*C3H4O4

C21H15ClF4N4O3*C3H4O4

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h; Solvent;84.5%
regorafenib
755037-03-7

regorafenib

4-{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide hydrochloride
835621-07-3

4-{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; 1,3-dioxane79%
With hydrogenchloride In tetrahydrofuran; 1,4-dioxane79%
With hydrogenchloride In tetrahydrofuran; 1,4-dioxane79%
With hydrogenchloride In tetrahydrofuran; 1,4-dioxane79%
With hydrogenchloride In tetrahydrofuran; 1,4-dioxane79%
regorafenib
755037-03-7

regorafenib

4-{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide phenylsulfonate
835621-09-5

4-{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide phenylsulfonate

Conditions
ConditionsYield
With benzenesulfonic acid In ethanol69%
regorafenib
755037-03-7

regorafenib

benzenesulfonic acid
98-11-3

benzenesulfonic acid

4-{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide phenylsulfonate
835621-09-5

4-{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide phenylsulfonate

Conditions
ConditionsYield
In ethanol Heating;69%
In ethanol Heating;69%
In ethanol Heating / reflux;69%
In ethanol Heating;69%
regorafenib
755037-03-7

regorafenib

4-{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide mesylate
835621-08-4

4-{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide mesylate

Conditions
ConditionsYield
With methanesulfonic acid In ethanol
regorafenib
755037-03-7

regorafenib

methanesulfonic acid
75-75-2

methanesulfonic acid

4-{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide mesylate
835621-08-4

4-{4-[3-(4-chloro-3-trifluoromethylphenyl)-ureido]-3-fluorophenoxy}-pyridine-2-carboxylic acid methylamide mesylate

Conditions
ConditionsYield
In ethanol
In ethanol
In ethanol
In ethanol
regorafenib
755037-03-7

regorafenib

4-[4({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)-3-fluorophenoxy]-N-methylpyridine-2-carboxamide monohydrate
1019206-88-2

4-[4({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)-3-fluorophenoxy]-N-methylpyridine-2-carboxamide monohydrate

Conditions
ConditionsYield
With water In acetone Product distribution / selectivity;
With water In acetonitrile at 25℃; for 168h; Product distribution / selectivity;
With water In ethanol at -20℃; Product distribution / selectivity;
regorafenib
755037-03-7

regorafenib

2-hydroxyethanesulfonic acid
107-36-8

2-hydroxyethanesulfonic acid

regorafenib isethionate salt

regorafenib isethionate salt

Conditions
ConditionsYield
In water; ethyl acetate at 40℃; for 2h; Solvent; Temperature;
regorafenib
755037-03-7

regorafenib

ethanesulfonic acid
594-45-6

ethanesulfonic acid

regorafenib ethanesulfonic acid salt

regorafenib ethanesulfonic acid salt

Conditions
ConditionsYield
In water; ethyl acetate at 50℃; for 2h; Solvent; Temperature;
regorafenib
755037-03-7

regorafenib

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

regorafenib p-toluenesulfonate salt

regorafenib p-toluenesulfonate salt

Conditions
ConditionsYield
In propan-1-ol at 50℃; for 4h; Solvent; Temperature;
regorafenib
755037-03-7

regorafenib

A

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide
757251-39-1

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide

B

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

Conditions
ConditionsYield
In water; acetonitrile at 80℃; for 72h;
regorafenib
755037-03-7

regorafenib

A

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide
757251-39-1

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide

B

1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-4-hydroxyphenyl)urea
1333390-56-9

1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-4-hydroxyphenyl)urea

C

4-chloro-3-trifluoromethyl-aniline
320-51-4

4-chloro-3-trifluoromethyl-aniline

Conditions
ConditionsYield
With hydrogenchloride at 80℃; for 5h;
...Expand
regorafenib
755037-03-7

regorafenib

A

1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-4-hydroxyphenyl)urea
1333390-56-9

1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-4-hydroxyphenyl)urea

B

C21H15ClF4N4O4

C21H15ClF4N4O4

Conditions
ConditionsYield
With dihydrogen peroxide In water at 20℃; for 144h;

Regorafenib Specification

The 4-[4-({[4-Chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)-3-fluorophenoxy]-N-methylpyridine-2-carboxamide with CAS registry number of 755037-03-7 is also called Regorafenib. Its systematic name is called 4-(4-(((4-chloro-3-(trifluoromethyl)phenyl)carbamoyl}amino)-3-fluorophenoxy)-N-methylpyridine-2-carboxamide.

Physical properties about this chemical are: (1) ACD/LogP: 4.49; (2) # of Rule of 5 Violations: 0; (3) ACD/LogD (pH 5.5): 4.48; (4) ACD/LogD (pH 7.4): 4.48; (5) ACD/BCF (pH 5.5): 1507.8; (6) ACD/BCF (pH 7.4): 1506.05; (7) ACD/KOC (pH 5.5): 6556.04; (8) ACD/KOC (pH 7.4): 6548.43; (9) #H bond acceptors: 7; (10) #H bond donors: 3; (11) #Freely Rotating Bonds: 5; (12) Polar Surface Area: 65.98 Å2; (13) Index of Refraction: 1.615; (14) Molar Refractivity: 113.09 cm3; (15) Molar Volume: 323.6 cm3; (16) Polarizability: 44.83×10-24 cm3; (17) Surface Tension: 50.7 dyne/cm ; (18) Density: 1.491 g/cm3; (19) Flash Point: 264.3 °C ; (20) Enthalpy of Vaporization: 78.48 kJ/mol ; (21) Boiling Point: 513.4 °C at 760 mmHg; (22) Vapour Pressure: 1.19E-10 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1) InChI: InChI=1S/C21H15ClF4N4O3/c1-27-19(31)18-10-13(6-7-28-18)33-12-3-5-17(16(23)9-12)30-20(32)29-11-2-4-15(22)14(8-11)21(24,25)26/h2-10H,1H3,(H,27,31)(H2,29,30,32).

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