Dabrafenib
Katalognummer B601069
Molekulargewicht: 519.6 g/mol
InChI-Schlüssel: BFSMGDJOXZAERB-UHFFFAOYSA-N
Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.
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
196 mg
Type
reactant
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
|
|
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Quantity
|
8 mL
|
|
Type
|
reactant
|
|
Smiles
|
N
|
|
Name
|
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
solvent
|
|
Smiles
|
CO
|
Step Two
[Compound]
|
Name
|
raw material
|
|
Quantity
|
0 (± 1) mol
|
|
Type
|
reactant
|
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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. |
