301836-35-1

Basic information

• Product Name: 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid
• Synonyms: 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid;4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-iMidazol-2-y;4-[4-(1,3-benzodioxol-5-yl)-5-(2-pyridinyl)-1H-imidazol-2-yl]Benzoic acid
• CAS NO: 301836-35-1
• Molecular Formula: C₂₂H₁₅N₃O₄
• Molecular Weight: 385.3722
• Mol File: 301836-35-1.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid(301836-35-1)
• EPA Substance Registry System: 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid(301836-35-1)

Safety Data

• Hazardous Substances Data: 301836-35-1(Hazardous Substances Data)

Usage

General Description

4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid is a compound with a complex chemical structure. It contains benzene rings and heterocyclic moieties such as pyridine and imidazole. The presence of benzo[d][1,3]dioxol-5-yl indicates the presence of a benzodioxole ring in the structure. 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid belongs to the class of benzoic acids and is commonly used in medicinal chemistry and drug discovery research. It may have potential pharmaceutical applications due to its diverse structural features and biological activities. Its chemical properties make it a subject of interest for further studies in the fields of organic synthesis, medicinal chemistry, and drug development.

Synthetic route

4-(4-Benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-1H-imidazol-2-yl)benzonitrile (301836-34-0) → 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1)

Conditions	Yield
With hydrogenchloride for 36h; Heating;

2-hydroxyimino-2-(2-pyridyl)-(2,3-methylenedioxy)-acetophenone → 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: NH4OAc / acetic acid / 36 h / Heating 2: P(OEt)3 / dimethylformamide / 1 h / 110 °C 3: conc. HCl / 36 h / Heating View Scheme

2-(4-cyanophenyl)-4-(3,4-methylenedioxyphenyl)-N-1-hydroxy-5-(2-pyridyl)-imidazole (301836-33-9) → 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: P(OEt)3 / dimethylformamide / 1 h / 110 °C 2: conc. HCl / 36 h / Heating View Scheme

4-cyanobenzaldehyde (105-07-7) + resin-bound phenylboronic acid → 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: NH4OAc / acetic acid / 36 h / Heating 2: P(OEt)3 / dimethylformamide / 1 h / 110 °C 3: conc. HCl / 36 h / Heating View Scheme

oxalyl dichloride (79-37-8) + 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1) → 4-(4-Benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-1H-imidazol-2-yl)benzoyl chloride

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide

oxalyl dichloride (79-37-8) + 4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1) → 4-[4-(3,4-methylenedioxyphenyl)-5-(2-pyridyl)-1H-imidazol-2-yl]benzoyl chloride hydrochloride

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide

4-(4-(benzo[d][1,3]dioxol-5-yl)-5-(pyridin-2-yl)-1H-imidazol-2-yl)benzoic acid (301836-35-1) → SB-431542

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane; N,N-dimethyl-formamide 2: ammonium hydroxide / tetrahydrofuran View Scheme

Upstream product

• 105-07-7 4-cyanobenzaldehyde 
• 301836-33-9 2-(4-cyanophenyl)-4-(3,4-methylenedioxyphenyl)-N-1-hydroxy-5-(2-pyridyl)-imidazole 
• 301836-34-0 4-(4-Benzo[1,3]dioxol-5-yl-5-pyridin-2-yl-1H-imidazol-2-yl)benzonitrile 

Relevant articles and documents

Identification of novel inhibitors of the transforming growth factor β1 (TGF-β1) type 1 receptor (ALK5)

Screening of our internal compound collection for inhibitors of the transforming growth factor β1 (TGF-β1) type I receptor (ALK5) identified several hits. Optimization of the dihydropyrroloimidazole hit 2 by introduction of a 2-pyridine and 3,4-methylenedioxyphenyl group gave 7, a selective ALK5 inhibitor. With this information, optimization of the triarylimidazole hit 8 gave the selective inhibitor 14, which inhibits TGF-β1-induced fibronectin mRNA formation while displaying no measurable cytotoxicity in the 48 h XTT assay.