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1195765-45-7

Basic Information
CAS No.: 1195765-45-7
Name: N-[3-[5-(2-Amino-4-pyrimidinyl)-2-(tert-butyl)-4-thiazolyl]-2-fluorophenyl]-2,6-difluorobenzenesulfonamide
Article Data: 12
Molecular Structure:
Molecular Structure of 1195765-45-7 (N-[3-[5-(2-Amino-4-pyrimidinyl)-2-(tert-butyl)-4-thiazolyl]-2-fluorophenyl]-2,6-difluorobenzenesulfonamide)
Formula: C23H20F3N5O2S2
Molecular Weight: 519.571
Synonyms: N-[3-[5-(2-Amino-4-pyrimidinyl)-2-(tert-butyl)-4-thiazolyl]-2-fluorophenyl]-2,6-difluorobenzenesulfonamide;N-[3-[5-(2-Amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-4-thiazolyl]-2-fluorophenyl]-2,6-difluorobenzenesulfonamide;
EINECS: 689-166-9
Density: 1.444 g/cm3
Boiling Point: 653.726 °C at 760 mmHg
Flash Point: 349.161 °C
PSA: 148.21000
LogP: 6.44880
Synthetic route
1195768-23-0

N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1 ,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide

1195765-45-7

dabrafenib

Conditions
ConditionsYield
With ammonium hydroxide In water at 20 - 103℃; Product distribution / selectivity; sealed tube;88%
With ammonium hydroxide at 98 - 103℃; for 2h; Sealed tube;88%
With ammonium hydroxide at 20 - 103℃; Reagent/catalyst; Autoclave;88%
60230-37-7

2,6-difluorobenzene-1-sulfonamide

4-(4-(3-bromo-2-fluorophenyl)-2-(tert-butyl)thiazol-5-yl)pyrimidin-2-amine

1195765-45-7

dabrafenib

Conditions
ConditionsYield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N,N,N',N'-tetramethylguanidine In dimethyl sulfoxide at 55℃; for 40h; Inert atmosphere; Glovebox; Irradiation;57%
60230-36-6

2,6-difluorobenzene-1-sulfonyl chloride

1195765-45-7

dabrafenib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: pyridine / dichloromethane / 15 - 25 °C
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 3 °C
3.1: N-Bromosuccinimide / dichloromethane / 10 - 20 °C
3.2: 2.5 h / 10 - 75 °C
4.1: ammonium hydroxide / water / 20 - 103 °C / sealed tube
View Scheme
Multi-step reaction with 4 steps
1.1: pyridine / dichloromethane / 15 - 25 °C
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 3 °C
3.1: N-Bromosuccinimide / dichloromethane / 10 - 20 °C
3.2: 2.5 h / 10 - 75 °C
4.1: ammonium hydroxide / 2 h / 98 - 103 °C / Sealed tube
View Scheme
Multi-step reaction with 5 steps
1: pyridine / dichloromethane / 15 - 25 °C
2: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 3 °C
3: N-Bromosuccinimide / dichloromethane / 10 - 20 °C
4: ethyl acetate; N,N-dimethyl acetamide / 10 - 75 °C
5: ammonium hydroxide / 20 - 103 °C / Autoclave
View Scheme
1195768-18-3

methyl 3-amino-2-fluoro-benzoate

1195765-45-7

dabrafenib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: pyridine / dichloromethane / 15 - 25 °C
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 3 °C
3.1: N-Bromosuccinimide / dichloromethane / 10 - 20 °C
3.2: 2.5 h / 10 - 75 °C
4.1: ammonium hydroxide / water / 20 - 103 °C / sealed tube
View Scheme
Multi-step reaction with 6 steps
1: pyridine / dichloromethane / 20 °C
2: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / Cooling with ice
3: N-Bromosuccinimide / N,N-dimethyl acetamide / 0.25 h / 20 °C
4: N,N-dimethyl acetamide / 20 - 60 °C
5: N,N-dimethyl acetamide / 60 - 80 °C
6: ammonia / methanol / 24 h / 90 °C / Sealed tube
View Scheme
Multi-step reaction with 4 steps
1.1: pyridine / dichloromethane / 15 - 25 °C
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 3 °C
3.1: N-Bromosuccinimide / dichloromethane / 10 - 20 °C
3.2: 2.5 h / 10 - 75 °C
4.1: ammonium hydroxide / 2 h / 98 - 103 °C / Sealed tube
View Scheme
1195768-19-4

3-(2,6-difluorobenzenesulfonamido)-2-fluorobenzoic acid methyl ester

1195765-45-7

dabrafenib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 3 °C
2.1: N-Bromosuccinimide / dichloromethane / 10 - 20 °C
2.2: 2.5 h / 10 - 75 °C
3.1: ammonium hydroxide / water / 20 - 103 °C / sealed tube
View Scheme
Multi-step reaction with 5 steps
1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / Cooling with ice
2: N-Bromosuccinimide / N,N-dimethyl acetamide / 0.25 h / 20 °C
3: N,N-dimethyl acetamide / 20 - 60 °C
4: N,N-dimethyl acetamide / 60 - 80 °C
5: ammonia / methanol / 24 h / 90 °C / Sealed tube
View Scheme
Multi-step reaction with 3 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 3 °C
2.1: N-Bromosuccinimide / dichloromethane / 10 - 20 °C
2.2: 2.5 h / 10 - 75 °C
3.1: ammonium hydroxide / 2 h / 98 - 103 °C / Sealed tube
View Scheme
1042055-86-6

methyl 3-((tert-butoxycarbonyl)amino)-2-fluorobenzoate

1195765-45-7

dabrafenib

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
2: pyridine / dichloromethane / 20 °C
3: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / Cooling with ice
4: N-Bromosuccinimide / N,N-dimethyl acetamide / 0.25 h / 20 °C
5: N,N-dimethyl acetamide / 20 - 60 °C
6: N,N-dimethyl acetamide / 60 - 80 °C
7: ammonia / methanol / 24 h / 90 °C / Sealed tube
View Scheme
1195768-20-7

N-(3-(2-(2-chloropyrimidin-4-yl)acetyl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide

1195765-45-7

dabrafenib

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-Bromosuccinimide / N,N-dimethyl acetamide / 0.25 h / 20 °C
2: N,N-dimethyl acetamide / 20 - 60 °C
3: N,N-dimethyl acetamide / 60 - 80 °C
4: ammonia / methanol / 24 h / 90 °C / Sealed tube
View Scheme
Multi-step reaction with 2 steps
1.1: N-Bromosuccinimide / dichloromethane / 10 - 20 °C
1.2: 2.5 h / 10 - 75 °C
2.1: ammonium hydroxide / 2 h / 98 - 103 °C / Sealed tube
View Scheme
Multi-step reaction with 3 steps
1: N-Bromosuccinimide / dichloromethane / 10 - 20 °C
2: ethyl acetate; N,N-dimethyl acetamide / 10 - 75 °C
3: ammonium hydroxide / 20 - 103 °C / Autoclave
View Scheme

N-(3-(2-bromo-2-(2-chloropyrimidin-4-yl)acetyl)-2-fluorophenyl)-2,6-difluorobenzenesulfonamide

1195765-45-7

dabrafenib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N,N-dimethyl acetamide / 20 - 60 °C
2: N,N-dimethyl acetamide / 60 - 80 °C
3: ammonia / methanol / 24 h / 90 °C / Sealed tube
View Scheme
Multi-step reaction with 2 steps
1: ethyl acetate; N,N-dimethyl acetamide / 10 - 75 °C
2: ammonium hydroxide / 20 - 103 °C / Autoclave
View Scheme
206551-41-9

2-fluoro-3-bromobenzoic acid methyl ester

1195765-45-7

dabrafenib

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 90 °C / Sealed tube; Inert atmosphere
2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
3: pyridine / dichloromethane / 20 °C
4: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / Cooling with ice
5: N-Bromosuccinimide / N,N-dimethyl acetamide / 0.25 h / 20 °C
6: N,N-dimethyl acetamide / 20 - 60 °C
7: N,N-dimethyl acetamide / 60 - 80 °C
8: ammonia / methanol / 24 h / 90 °C / Sealed tube
View Scheme
Multi-step reaction with 4 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C
2.1: N-Bromosuccinimide / N,N-dimethyl acetamide / 0.25 h / 20 °C
2.2: 2 h / 120 °C
3.1: ammonium hydroxide / 1,4-dioxane / 24 h / 90 °C / Sealed tube
4.1: (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N,N,N',N'-tetramethylguanidine / dimethyl sulfoxide / 40 h / 55 °C / Inert atmosphere; Glovebox; Irradiation
View Scheme
161957-56-8

3-bromo-2-fluorobenzoic acid

1195765-45-7

dabrafenib

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: sulfuric acid / 1 h / Reflux
2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; caesium carbonate / 90 °C / Sealed tube; Inert atmosphere
3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
4: pyridine / dichloromethane / 20 °C
5: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / Cooling with ice
6: N-Bromosuccinimide / N,N-dimethyl acetamide / 0.25 h / 20 °C
7: N,N-dimethyl acetamide / 20 - 60 °C
8: N,N-dimethyl acetamide / 60 - 80 °C
9: ammonia / methanol / 24 h / 90 °C / Sealed tube
View Scheme
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1195768-06-9
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Specification

The Dabrafenib, with the CAS registry number 1195765-45-7, is also known as N-[3-[5-(2-Amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-4-thiazolyl]-2-fluorophenyl]-2,6-difluorobenzenesulfonamide. This chemical's molecular formula is C23H20F3N5O2S2 and molecular weight is 519.56. What's more, its systematic name is N-[3-[5-(2-Aminopyrimidin-4-yl)-2-tert-butyl-thiazol-4-yl]-2-fluoro-phenyl]-2,6-difluoro-benzenesulfonamide. 

Physical properties of Dabrafenib are: (1)ACD/LogP: 2.944; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.91; (4)ACD/LogD (pH 7.4): 2.05; (5)ACD/BCF (pH 5.5): 93.21; (6)ACD/BCF (pH 7.4): 13.09; (7)ACD/KOC (pH 5.5): 871.91; (8)ACD/KOC (pH 7.4): 122.45; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 147.48 Å2; (13)Index of Refraction: 1.626; (14)Molar Refractivity: 127.358 cm3; (15)Molar Volume: 359.868 cm3; (16)Polarizability: 50.489×10-24cm3; (17)Surface Tension: 61.008 dyne/cm; (18)Density: 1.444 g/cm3; (19)Flash Point: 349.161 °C; (20)Enthalpy of Vaporization: 96.299 kJ/mol; (21)Boiling Point: 653.726 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(C)(C)c1nc(c(s1)c2ccnc(n2)N)c3cccc(c3F)NS(=O)(=O)c4c(cccc4F)F
(2)Std. InChI: InChI=1S/C23H20F3N5O2S2/c1-23(2,3)21-30-18(19(34-21)16-10-11-28-22(27)29-16)12-6-4-9-15(17(12)26)31-35(32,33)20-13(24)7-5-8-14(20)25/h4-11,31H,1-3H3,(H2,27,28,29)
(3)Std. InChIKey: BFSMGDJOXZAERB-UHFFFAOYSA-N