Synthesis routes of Dabrafenib

Dabrafenib

Numéro de catalogue B601069

: 1195765-45-7

Poids moléculaire: 519.6 g/mol

Clé InChI: BFSMGDJOXZAERB-UHFFFAOYSA-N

Attention: Uniquement pour un usage de recherche. Non destiné à un usage humain ou vétérinaire.

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Patent

US08642759B2

Procedure details

Following a procedure analogous to the procedure described in Example 51, Step B using 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 ammonia in methanol 7M (8 ml, 56.0 mmol) and heating to 90° C. for 24 h, the title compound, N-{3-[5-(2-amino-4-pyrimidinyl)-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide was obtained (94 mg, 47% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 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). MS (ESI): 519.9 [M+H]+.

Name

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

Quantity

196 mg

Type

reactant

Reaction Step One

Name

ammonia

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

methanol

Quantity

8 mL

Type

reactant

Reaction Step Three

Name

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

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

Step Two

Name	ammonia
Quantity	0 (± 1) mol
Type	reactant
Smiles	N

Step Three

Name	methanol
Quantity	8 mL
Type	reactant
Smiles	CO

Conditions

Temperature

Control Type	UNSPECIFIED
Setpoint	90 °C

Other

Conditions are dynamic	1
Details	See reaction.notes.procedure_details.

Outcomes

Product

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

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.