31349-48-1

Usage

Uses

Used in Pharmaceutical Synthesis:
1-Methyl-5-nitro-2-benzimidazolebutyric acid is used as a key intermediate in the synthesis of various pharmaceuticals for its versatile chemical structure and functional groups that can be further modified for drug development.
Used in Research Chemicals:
It serves as a research chemical, aiding scientists in understanding its chemical properties and potential interactions with biological systems, which is crucial for advancing knowledge in medicinal chemistry.
Used in Medical Treatments:
1-Methyl-5-nitro-2-benzimidazolebutyric acid is used as a potential therapeutic agent for various medical conditions due to its studied anti-inflammatory and antioxidant properties. It is particularly being investigated for its potential in treating cancer, inflammation, and cardiovascular diseases, where its specific mechanisms of action could offer new avenues for treatment.

Upstream product

• 108-55-4 glutaric anhydride, 
• 369-36-8 6-fluoro-3-nitroaniline 
• 74-89-5 methylamine 
• 451459-95-3 5-(2-fluoro-5-nitroanilino)-5-oxopentanoic acid 

Downstream Products

• 3543-73-5 ethyl 4‐(5‐amino‐1‐methyl‐1H‐benzo[d]imidazol‐2‐yl)butanoate 
• 3543-74-6 4-{5-[bis-(2-hydroxyl-ethyl)-amino]-1-methyl-1H-benzoimidazol-2yl}-butyric acid ethyl ester 
• 3543-75-7 bendamustine hydrochloride 
• 16506-27-7 bendamustine 
• 3543-72-4 4‐(1‐methyl‐5‐nitro‐1H‐benzoimidazol‐2‐yl)butyric acid ethyl ester 

Relevant academic research and scientific papers

Process for preparation of Bendamustine

The present invention relates to a method for preparation of alkyl 4-[5-[bis(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazol-2-yl]butanoate (7) from 2-fluoro-5-nitroaniline, comprising the steps of: a) conversion of 2-fluoro-5-nitroaniline to 5-(2-fluoro-5-nitroanilino)-5-oxopentanoic acid (1) using glutaric anhydride, conversion of compound (1) to methylammonium 5-[2-(methylamino)-5-nitroanilino]-5-oxopentanoate (2) using methylamine; conversion of compound (2) to 5-[2-(methylamino)-5-nitroanilino]-5-oxopentanoic acid (3) and condensation of compound (3) to 4-(1-methyl-5-nitro-1H-benzimidazol-2-yl)butanoic acid (4), b) esterification of the product (4) of step a) to alkyl 4-(1-methyl-5-nitro1H-benzimidazol-2-yl)butanoate (5), c) reduction of the product of step b) to alkyl 4-(5-amino-1-methyl-1H-benzimidazol-2-yl)butanoate (6), and d) conversion of the product of step c) to alkyl 4-[5-[bis(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazol-2-yl]butanoate (7).

PROCESS FOR THE PREPARATION OF BENDAMUSTINE

The present invention relates to a method for preparation of alkyl 4-[5-[bis(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazol-2-yl]butanoate (7) from 2-fluoro-5-nitroaniline, comprising the steps of: (a) conversion of 2-fluoro-5-nitroaniline to 5-(2-fluoro-5-nitroanilino)-5-oxopentanoic acid (1) using glutaric anhydride, conversion of compound (1) to methylammonium 5-[2-(methylamino)-5-nitroanilino]-5-oxopentanoate (2) using methylamine; conversion of compound (2) to 5-[2-(methylamino)-5-nitroanilino]-5-oxopentanoic acid (3) and condensation of compound (3) to 4-(1-methyl-5-nitro-1H-benzimidazol-2-yl)butanoic acid (4); (b) esterification of the product (4) of step a) to alkyl 4-(1-methyl-5-nitro1H-benzimidazol-2-yl)butanoate (5); (c) reduction of the product of step b) to alkyl 4-(5-amino-1-methyl-1H-benzimidazol-2-yl)butanoate (6), and (d) conversion of the product of step c) to alkyl 4-[5-[bis(2-hydroxyethyl)amino]-1-methyl-1H-benzimidazol-2-yl]butanoate (7)