5-((4-Bromo-2-chlorophenyl)amino)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylic acid

Numéro de catalogue: B1317276

Numéro CAS: 606144-04-1

Poids moléculaire: 398.61 g/mol

Clé InChI: XAAPQRFIXGDKPZ-UHFFFAOYSA-N

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

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Vue d'ensemble

1. Description

6. Comparaison avec des composés similaires

2. Méthodes de préparation

7. Propriétés

3. Analyse des réactions chimiques

8. Synthesis routes and methods

4. Applications de recherche scientifique

9. Avertissement

5. Mécanisme d'action

Description

5-((4-Bromo-2-chlorophenyl)amino)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylic acid is a complex organic compound that belongs to the class of benzimidazole derivatives. These compounds are known for their diverse biological activities and are widely used in medicinal chemistry for the development of therapeutic agents.

Méthodes De Préparation

Synthetic Routes and Reaction Conditions

The synthesis of 5-((4-Bromo-2-chlorophenyl)amino)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylic acid typically involves multiple steps, starting from commercially available precursors. One common method involves the cyclization of amido-nitriles in the presence of a nickel catalyst, followed by proto-demetallation, tautomerization, and dehydrative cyclization . The reaction conditions are mild and can accommodate a variety of functional groups, including aryl halides and heterocycles .

Industrial Production Methods

Industrial production methods for this compound are not widely documented, but they likely involve similar synthetic routes with optimizations for large-scale production. These optimizations may include the use of continuous flow reactors and automated synthesis platforms to improve yield and reduce production costs.

Analyse Des Réactions Chimiques

Types of Reactions

5-((4-Bromo-2-chlorophenyl)amino)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylic acid can undergo various chemical reactions, including:

Oxidation: This reaction typically involves the use of oxidizing agents such as hydrogen peroxide or potassium permanganate.

Reduction: Common reducing agents include sodium borohydride and lithium aluminum hydride.

Substitution: This compound can participate in nucleophilic substitution reactions, often using reagents like sodium methoxide or potassium tert-butoxide.

Common Reagents and Conditions

The reactions mentioned above generally require specific conditions to proceed efficiently. For example, oxidation reactions may require acidic or basic conditions, while reduction reactions often occur under anhydrous conditions to prevent side reactions.

Major Products Formed

The major products formed from these reactions depend on the specific reagents and conditions used. For instance, oxidation may yield carboxylic acids or ketones, while reduction can produce alcohols or amines.

Applications De Recherche Scientifique

5-((4-Bromo-2-chlorophenyl)amino)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylic acid has several scientific research applications:

Chemistry: It is used as a building block for the synthesis of more complex molecules.

Biology: This compound is studied for its potential biological activities, including antimicrobial and anticancer properties.

Medicine: It is investigated for its potential use in developing new therapeutic agents for various diseases.

Industry: The compound is used in the development of functional materials and catalysts.

Mécanisme D'action

The mechanism of action of 5-((4-Bromo-2-chlorophenyl)amino)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylic acid involves its interaction with specific molecular targets and pathways. For example, it may inhibit certain enzymes or receptors, leading to the modulation of biological processes. The exact molecular targets and pathways can vary depending on the specific application and context of use .

Comparaison Avec Des Composés Similaires

Similar Compounds

Selumetinib: 5-(4-Bromo-2-chlorophenylamino)-4-fluoro-N-(2-hydroxyethoxy)-1-methyl-1H-benzo[d]imidazole-6-carboxamide.

Methyl 5-(4-bromo-2-chlorophenylamino)-4-fluoro-1H-benzo[d]imidazole-6-carboxylate .

Uniqueness

Compared to similar compounds, 5-((4-Bromo-2-chlorophenyl)amino)-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylic acid stands out due to its unique combination of substituents, which can confer distinct biological activities and chemical reactivity. This uniqueness makes it a valuable compound for research and development in various scientific fields.

Propriétés

IUPAC Name	6-(4-bromo-2-chloroanilino)-7-fluoro-3-methylbenzimidazole-5-carboxylic acid	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C15H10BrClFN3O2/c1-21-6-19-14-11(21)5-8(15(22)23)13(12(14)18)20-10-3-2-7(16)4-9(10)17/h2-6,20H,1H3,(H,22,23)	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	XAAPQRFIXGDKPZ-UHFFFAOYSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CN1C=NC2=C1C=C(C(=C2F)NC3=C(C=C(C=C3)Br)Cl)C(=O)O	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C15H10BrClFN3O2	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

DSSTOX Substance ID	DTXSID20582176	Source
Record name	5-(4-Bromo-2-chloroanilino)-4-fluoro-1-methyl-1H-benzimidazole-6-carboxylic acid
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID20582176
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	398.61 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

CAS No.	606144-04-1	Source
Record name	AZ-133266637
Source	ChemIDplus
URL	https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0606144041
Description	ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system.

Record name	5-(4-Bromo-2-chloroanilino)-4-fluoro-1-methyl-1H-benzimidazole-6-carboxylic acid
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID20582176
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Record name	AZ-133266637
Source	FDA Global Substance Registration System (GSRS)
URL	https://gsrs.ncats.nih.gov/ginas/app/beta/substances/D67NVR9LE7
Description	The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions.
Explanation	Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.

Synthesis routes and methods

Procedure details

To a stirred mixture of 6-amino-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester (6) (8.00 g, 34.16 mmol) and cesium carbonate (22.48 g, 68.31 mmol) in anhydrous anisole (76 mL) under nitrogen was added 4-bromo-2-chloroiodobenzene (1.60 g, 1.10 equiv., 4.88 mmol). The preformed catalyst, as prepared above, was then added to the mixture to provide a dark brown suspension, which was heated at 100±2° C., with stirring at 350 rpm. The reaction was monitored by HPLC analysis. After 41 hours, no 6-amino-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester (6) remained. The reaction mixture was cooled to about 80° C. and 1M sulfuric acid (40.99 mL 40.99 mmol) was added. Gas evolution was observed after 10 minutes and the rate of addition was controlled to moderate the effervescence. At the end of the addition the pH was between 7 and 8. Additional sulfuric acid (1M, 10.25 mL, 10.25 mmol) was then added to give mobile slurry with a pH of 0. The mixture was diluted with anisole (20 mL) and Celatom FW-14 filter agent was added. It was then filtered at about 80° C. through a water-wet pad of Celatom FW-14 filter agent and the cake was washed with anisole (1×40 mL+3×20 mL), then water (10 mL). The lower aqueous layer was separated and discarded and the organic layer was washed with 10% aqueous NaCl solution (2×40 mL). This was added to a sodium hydroxide (5.46 g, 68.3 mmol) in methanol (24 mL) and the mixture was heated at 65° C. with stirring. After 17.5 hours HPLC analysis indicated that the hydrolysis of the ester was complete and the slurry was cooled to 15° C., then filtered on a sinter. The solid was washed with water (4×24 mL), MTBE (24 mL), and acetonitrile (2×25 mL) and then dried at 45° C. in a vacuum oven to provide 11.07 g of 6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (7) as a fine pale brown solid (assay 93.7% by 1H NMR), actual wt 10.37 g (72.2% yield). 1H NMR (400 MHz, d6 DMSO) δ 3.85 (3H, s, NMe), 6.53 (1H, dd, J 9, 7, Ar—H), 7.27 (1H, dd, J 9, 2.5, Ar—H), 7.56 (1H, d, J 9, Ar—H), 7.97 (1H, s, Ar—H), 8.20 (1H, s, Ar—H), 11.5 (1H, s, CO2H). 13C NMR (100 MHz, d6 DMSO) δ 31 (CH3), 108 (CH, d, J 2), 109 (CH), 117 (C, d, J 6), 122 (C), 124 (C, d, J 7), 127 (C), 130 (C), 131 (C), 132 (C, d, J 9), 133 (C, d, J 11), 141 (C), 145 (CF, d, J 252), 146 (CH), 170 (C═O).

Name

anisole

Quantity

20 mL

Type

solvent

Reaction Step One

Name

6-amino-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester

Quantity

8 g

Type

reactant

Reaction Step Two

Name

cesium carbonate

Quantity

22.48 g

Type

reactant

Reaction Step Two

Name

anisole

Quantity

76 mL

Type

solvent

Reaction Step Two

Name

4-bromo-2-chloroiodobenzene

Quantity

1.6 g

Type

reactant

Reaction Step Three

Name

6-amino-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid methyl ester

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

sulfuric acid

Quantity

40.99 mL

Type

reactant

Reaction Step Five

Name

sulfuric acid

Quantity

10.25 mL

Type

reactant

Reaction Step Six

Name

sodium hydroxide

Quantity

5.46 g

Type

reactant

Reaction Step Seven

Name

methanol

Quantity

24 mL

Type

solvent

Reaction Step Seven

[Compound]

Name

ester

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Eight

Name

6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid

Yield

72.2%

Details

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