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Basic Information
CAS No.: 755037-03-7
Name: Regorafenib
Article Data: 30
Molecular Structure:
Molecular Structure of 755037-03-7 (Regorafenib)
Formula: C21H15ClF4N4O3
Molecular Weight: 482.822
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;
EINECS: 815-051-1
Density: 1.491 g/cm3
Melting Point: 206.0 to 210.0 °C
Boiling Point: 513.4 °C at 760 mmHg
Flash Point: 264.3 °C
Solubility: DMSO
PSA: 92.35000
LogP: 6.22570
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Synthetic route
757251-39-1

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

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4-chloro-3-trifluoromethyl-aniline

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Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 140℃; for 4h; Temperature; Green chemistry;96.8%
...Expand
757251-39-1

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

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S,S-dimethyl dithiocarbonate

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4-chloro-3-trifluoromethyl-aniline

755037-03-7

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Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide In tetrahydrofuran at 35℃; for 1.33333h; Green chemistry;96.2%
...Expand
757251-39-1

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

327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

755037-03-7

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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%
399-95-1

4-amino-3-fluorophenol

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
1338722-52-3

C12H16FNO

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
1338722-53-4

C11H14FNO

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
394-41-2

3-fluoro-4-nitrophenol

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
98-98-6

2-Picolinic acid

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

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
220000-87-3

4-chloro-N-methylpicolinamide

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
Raw Materials
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757251-39-1
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  • RegorafenibCAS NO.: 755037-03-7

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    RegorafenibCAS NO.: 755037-03-7

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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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