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molecular formula C23H20F3N5O2S2 B601069 Dabrafenib CAS No. 1195765-45-7

Dabrafenib

Cat. No. B601069
M. Wt: 519.6 g/mol
InChI Key: BFSMGDJOXZAERB-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US09365559B2

Procedure details

Add N-{3-[5-(2-chloro-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (196 mg, 0.364 mmol) and 7M methanol solution of ammonia (8 ml, 56 mmol) into a 25 mL autoclave, heat to 90° C. and react for 24 h; when the TLC shows the raw material is completely reacted, cool the above reaction system to room temperature, filter to get N-{3-[5-(2-amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide (i.e. Dabrafenib). 1H-NMR (400 MHz, DMSO-d6) δppm 10.83 (s, 1H), 7.93 (d, J=5.2 Hz, 1H), 7.55-7.70 (m, 1H), 7.35-7.43 (m, 1H), 7.31 (t, J=6.3 Hz, 1H), 7.14-7.27 (m, 3H), 6.70 (s, 2H), 5.79 (d, J=5.13 Hz, 1H), 1.35 (s, 9H).
Quantity
8 mL
Type
reactant
Reaction Step One
Quantity
0 (± 1) mol
Type
solvent
Reaction Step One
[Compound]
Name
raw material
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
Cl[C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:10][C:9]=2[C:17]2[C:18]([F:35])=[C:19]([NH:23][S:24]([C:27]3[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=3[F:34])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:5]=[CH:4][N:3]=1.[NH3:36]>CO>[NH2:36][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])=[N:10][C:9]=2[C:17]2[C:18]([F:35])=[C:19]([NH:23][S:24]([C:27]3[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=3[F:34])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=2)[CH:5]=[CH:4][N:3]=1

Inputs

Step One
Name
Quantity
196 mg
Type
reactant
Smiles
ClC1=NC=CC(=N1)C1=C(N=C(S1)C(C)(C)C)C=1C(=C(C=CC1)NS(=O)(=O)C1=C(C=CC=C1F)F)F
Name
Quantity
8 mL
Type
reactant
Smiles
N
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
CO
Step Two
Name
raw material
Quantity
0 (± 1) mol
Type
reactant
Smiles

Conditions

Temperature
Control Type
UNSPECIFIED
Setpoint
90 °C
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
react for 24 h
Duration
24 h
CUSTOM
Type
CUSTOM
Details
is completely reacted
TEMPERATURE
Type
TEMPERATURE
Details
cool the above reaction system to room temperature
FILTRATION
Type
FILTRATION
Details
filter

Outcomes

Product
Name
Type
product
Smiles
NC1=NC=CC(=N1)C1=C(N=C(S1)C(C)(C)C)C=1C(=C(C=CC1)NS(=O)(=O)C1=C(C=CC=C1F)F)F

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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