Synthesis routes of 5-((4-Bromo-2-chlorophenyl)amino)-4-fluoro-1-methyl-N-(2-(vinyloxy)ethoxy)-1H-benzo[d]imidazole-6-carboxamide

5-((4-Bromo-2-chlorophenyl)amino)-4-fluoro-1-methyl-N-(2-(vinyloxy)ethoxy)-1H-benzo[d]imidazole-6-carboxamide

Katalognummer B1376880

: 606144-05-2

Molekulargewicht: 483.7 g/mol

InChI-Schlüssel: GNDKPEUWKWSUMP-UHFFFAOYSA-N

Achtung: Nur für Forschungszwecke. Nicht für den menschlichen oder tierärztlichen Gebrauch.

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Patent

US07425637B2

Procedure details

Hydrochloric acid (14 mL, 1.0 M aqueous solution, 14 mmol) is added to a suspension of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-vinyloxy-ethoxy)-amide 29a (2.18 g, 4.50 mmol) in ethanol (50 mL) and the reaction mixture allowed to stir for 24 hours. The reaction mixture is concentrated to dryness by rotary evaporation and the solids partitioned between 3:1 ethyl acetate/tetrahydrofuran and saturated potassium carbonate. The aqueous phase is extracted with 3:1 ethyl acetate/tetrahydrofuran (3×), the combined organics dried (Na2SO4), and concentrated to provide 2.11 g (100%) 6-(4-bromo-2chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide as an off-white solid. MS ESI (+) m/z 457, 459 (M+, Br pattern) detected. 1H NMR (400 MHz, MeOH-d4) δ 8.26 (s, 1H), 7.78 (s, 1H), 7.57 (d, 1H), 7.24 (dd, 1H), 6.40 (dd, 1H), 3.86 (s, 3H), 3.79 (m, 2H), 3.49 (m, 2H). 19F NMR (376 MHz, MeOH-d4)-133.68 (s).

Name

Hydrochloric acid

Quantity

14 mL

Type

reactant

Reaction Step One

Name

6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-vinyloxy-ethoxy)-amide

Quantity

2.18 g

Type

reactant

Reaction Step One

Name

ethanol

Quantity

50 mL

Type

solvent

Reaction Step One

Name

6-(4-bromo-2chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide

Yield

100%

Identifiers

REACTION_CXSMILES

Cl.C([O:4][CH2:5][CH2:6][O:7][NH:8][C:9]([C:11]1[C:20]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:23]=2[Cl:29])=[C:19]([F:30])[C:14]2[N:15]=[CH:16][N:17]([CH3:18])[C:13]=2[CH:12]=1)=[O:10])=C>C(O)C>[OH:4][CH2:5][CH2:6][O:7][NH:8][C:9]([C:11]1[C:20]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:23]=2[Cl:29])=[C:19]([F:30])[C:14]2[N:15]=[CH:16][N:17]([CH3:18])[C:13]=2[CH:12]=1)=[O:10]

Inputs

Step One

Name	Hydrochloric acid
Quantity	14 mL
Type	reactant
Smiles	Cl

Name	6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-vinyloxy-ethoxy)-amide
Quantity	2.18 g
Type	reactant
Smiles	C(=C)OCCONC(=O)C1=CC2=C(N=CN2C)C(=C1NC1=C(C=C(C=C1)Br)Cl)F

Name	ethanol
Quantity	50 mL
Type	solvent
Smiles	C(C)O

Conditions

Stirring

Type	CUSTOM
Details	to stir for 24 hours
Rate	UNSPECIFIED
RPM	0

Other

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

Workups

CONCENTRATION

Type	CONCENTRATION
Details	The reaction mixture is concentrated to dryness by rotary evaporation

CUSTOM

Type	CUSTOM
Details	the solids partitioned between 3:1 ethyl acetate/tetrahydrofuran and saturated potassium carbonate

EXTRACTION

Type	EXTRACTION
Details	The aqueous phase is extracted with 3:1 ethyl acetate/tetrahydrofuran (3×)

DRY_WITH_MATERIAL

Type	DRY_WITH_MATERIAL
Details	the combined organics dried (Na2SO4)

CONCENTRATION

Type	CONCENTRATION
Details	concentrated

Outcomes

Product

Details

Reaction Time

24 h

Name	6-(4-bromo-2chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide
Type	product
Smiles	OCCONC(=O)C1=CC2=C(N=CN2C)C(=C1NC1=C(C=C(C=C1)Br)Cl)F

Measurements

Type	Value	Analysis
AMOUNT: MASS	2.11 g
YIELD: PERCENTYIELD	100%
YIELD: CALCULATEDPERCENTYIELD	102.4%

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.