51314-51-3

Usage

Uses

Used in Pharmaceutical Research and Synthesis:
1H-Benzimidazol-2-amine,N-butyl-(9CI) is utilized as a building block in the development of new drugs and biologically active compounds. Its unique structure and functional groups make it a valuable component in the design and synthesis of pharmaceutical agents targeting various therapeutic areas.
Used in Chemical Reactions:
As a reagent, 1H-Benzimidazol-2-amine,N-butyl-(9CI) plays a role in various chemical reactions, facilitating the synthesis of complex organic molecules. Its presence can influence the course of reactions and the formation of desired products, making it a useful tool in organic chemistry.
Used as a Starting Material:
1H-Benzimidazol-2-amine,N-butyl-(9CI) also serves as a starting material for the production of other organic compounds. Its versatility and the presence of reactive functional groups allow it to be transformed into a range of different molecules, expanding its utility in the chemical industry.
While the specific applications and industries for 1H-Benzimidazol-2-amine,N-butyl-(9CI) are not explicitly detailed in the provided materials, its role in pharmaceutical research, chemical reactions, and as a starting material for organic synthesis highlights its potential across various sectors, including drug development, chemical manufacturing, and materials science.

InChI:InChI=1/C11H15N3/c1-2-3-8-12-11-13-9-6-4-5-7-10(9)14-11/h4-7H,2-3,8H2,1H3,(H2,12,13,14)

Upstream product

• 109-73-9 N-butylamine 
• 95-54-5 1,2-diamino-benzene 
• 934-32-7 1H-benzimidazol-2-amine 
• 4857-06-1 2-chloro-1H-benzoimidazole 
• 2769-64-4 n-butyl isonitrile 
• 71-36-3 butan-1-ol 
• 87504-17-4 2-cyclohexylbenzimidazo<1,2-d><1,2,4>thiadiazol-3(2H)-one 
• 85997-29-1 2-butylbenzimidazo<1,2-d><1,2,4>thiadiazol-3(2H)-one 
• 98154-63-3 2-ethyl-1,2,4-thiadiazolo[4,5-a]benzimidazole-3(2H)-one 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 
• 72885-92-8 2-phenyl-2H-benzo[4,5]imidazo[1,2-d][1,2,4]thiadiazol-3-one 
• 43181-78-8 1-benzyl-2-chlorobenzimidazole 

Relevant academic research and scientific papers

The high-pressure S(N)AR reaction of N-p-fluorobenzyl-2- chlorobenzimidazole with amines; an approach to norastemizole and analogues

N-p-fluorobenzyl-2-chlorobenzimidazole was treated under hyperbaric conditions with a variety of primary and secondary amines. The resulting S(N)Ar reaction proceeded smoothly to produce excellent yields of adducts in most cases. This methodology provides rapid access to astemizole, norastemizole and related analogues.

Nucleophilic Substitution at the Guanidine Carbon Center via Guanidine Cyclic Diimide Activation

Despite the electron-deficient nature of the guanidine carbon centers, nucleophilic reactions at these sites have been underdeveloped because of the resonance stabilization of the guanidine group. We propose a guanidine C-N bond substitution strategy entailing the formation of guanidine cyclic diimide (GCDI) structures, which effectively destabilize the resonance structure of the guanidine group. In the presence of acid additives, the guanidine carbon center of GCDIs undergoes nucleophilic substitution reactions with various amines and alcohols.

Identification and optimization of 2-aminobenzimidazole derivatives as novel inhibitors of TRPC4 and TRPC5 channels

Background and Purpose Transient receptor potential canonical (TRPC) channels play important roles in a broad array of physiological functions and are involved in various diseases. However, due to a lack of potent subtype-specific inhibitors the exact roles of TRPC channels in physiological and pathophysiological conditions have not been elucidated. Experimental Approach Using fluorescence membrane potential and Ca2+ assays and electrophysiological recordings, we characterized new 2-aminobenzimidazole-based small molecule inhibitors of TRPC4 and TRPC5 channels identified from cell-based fluorescence high-throughput screening. Key Results The original compound, M084, was a potent inhibitor of both TRPC4 and TRPC5, but was also a weak inhibitor of TRPC3. Structural modifications of the lead compound resulted in the identification of analogues with improved potency and selectivity for TRPC4 and TRPC5 channels. The aminobenzimidazole derivatives rapidly inhibited the TRPC4- and TRPC5-mediated currents when applied from the extracellular side and this inhibition was independent of the mode of activation of these channels. The compounds effectively blocked the plateau potential mediated by TRPC4-containing channels in mouse lateral septal neurons, but did not affect the activity of heterologously expressed TRPA1, TRPM8, TRPV1 or TRPV3 channels or that of the native voltage-gated Na+, K+ and Ca2+ channels in dissociated neurons. Conclusions and Implications The TRPC4/C5-selective inhibitors developed here represent novel and useful pharmaceutical tools for investigation of physiological and pathophysiological functions of TRPC4/C5 channels.

Use of primary amines for the selective n-alkylation of anilines by a reusable heterogeneous catalyst

Traditionally, anilines can be alkylated with reactive alkyl halides but now more safe reagents such as alcohols or even amines can be used. To overcome the limits of homogeneous catalysis for aniline N-alkylation, we have developed a protocol that employs simple Pd/C as a heterogeneous catalyst under microwave dielectric heating. The process, based on the easy Pd-mediated oxidation of primary amines to imines followed by aniline addition, is characterized by a high atom economy as ammonia is the only other product of the reaction. This kind of aniline alkylation with amines has been carried out both in ionic liquid medium using [bmim]PF6 or in a more traditional solvent such as THF where the catalyst could be successfully recycled more times. The reusability of the catalyst was further confirmed by using material recycled from the amination in a standard alkene hydrogenation without loss of efficiency. Georg Thieme Verlag Stuttgart New York.

Synthesis, biological evaluation and molecular modeling of substituted 2-aminobenzimidazoles as novel inhibitors of acetylcholinesterase and butyrylcholinesterase

A series of novel 2-aminobenzimidazole derivatives were synthesized under microwave irradiation. Their biological activities were evaluated on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). A number of the 2-aminobenzimidazole derivatives showed good inhibitory activities to AChE and BuChE. Among them, compounds 9, 12 and 13 were found to be >25-fold more selective for BuChE than AChE. No evidence of cytotoxicity was observed by MTT assay in PC12 cells or HepG2 cells exposed to 100 μM of the compounds. Molecular modeling studies indicate that the benzimidazole moiety of compounds 9, 12 and 13 forms a face-to-face π-π stacking interaction in a 'sandwich' form with the indole ring of Trp82 (4.09 A?) in the active gorge, and compounds 12 and 13 form a hydrogen bond with His438 at the catalytic site of BuChE. In addition, compounds 12 and 13 fit well into the hydrophobic pocket formed by Ala328, Trp430 and Tyr332 of BuChE. Our data suggest the 2-aminobenzimidazole drugs as promising new selective inhibitors for AChE and BuChE, potentially useful to treat neurodegenerative diseases.

Cobalt-catalyzed oxidative isocyanide insertion to amine-based bisnucleophiles: Diverse synthesis of substituted 2-aminobenzimidazoles, 2-aminobenzothiazoles, and 2-aminobenzoxazoles

Cobalt catalysis: Synthesis of substituted 2-aminobenzimidazoles, 2-aminobenzothiazoles, and 2-aminobenzoxazoles was achieved by using cobalt(II) acetate catalyzed isocyanide insertion to o-diaminobenzene, 2-aminobenzenethiol, and 2-aminophenol derivatives in 1,4-dioxane (see scheme). It was found that the reaction proceeded efficiently to give the desired products in up to 95 % isolated yields by C-N and C-S (O, N) formation in a single step. Copyright

Regioselective N-alkylation of 2-aminoimidazoles with alcohols to 2-(N-Alkylamino)imidazoles catalyzed by the [Cp*IrCl2] 2/K2CO3 system

The direct N-alkylation of 2-aminoimidazoles to give the corresponding 2-(N-alkylamino)imidazoles was accomplished using alcohols as alkylating agents in the presence of a [Cp*IrCl2]2/K 2CO3 system. The iridium-catalyzed regioselective reaction is simple, efficient, general, and environmentally benign. The direct N-alkylation of 2-aminoimidazoles to give the corresponding 2-(N-alkylamino) imidazoles was accomplished using alcohols as alkylating agents in the presence of a [Cp*IrCl2]2/K2CO3 system. The iridium-catalyzed regioselective reaction is simple, efficient, general, and environmentally benign. Copyright

Fission of 1,2,4-Thiadiazol-3-ones by Triphenylphosphane: Triphenylphosphonio Thioimidazolates and Their Consecutive Reactions

Treatment of benzimidazothiadiazol-3(2H)-ones (1) and imidazothiadiazol-3(2H)-ones (17) with triphenylphosphan leads to the liberation of isocyanate and the formation of triphenylphosphonio-thiobenzimidazolat (4) and triphenylphosphonio-thioimidazolat (18), respectively. 2,4-Diphenyl-5-phenylimino-1,2,4-thiadiazol-3-one (23) is desulfurized with Ph3P and decomposed into phenyl isocyanate and diphenylcarbodiimide whereas the N-unsubstituted imino-thiadiazol-3-one (25) is attacked at the exocyclic imino group by Ph3P to give the N-phosphoranylidene thiourea (26).The structure of 4 can be rationalized as a dynamic system between polar and apolar valence isomeres.Reactions of 1 and 17 with cyanates, isocyanates, carbon disulfide, acetic anhydride, amines, benzyl chloride, grignard compounds, and CH acidic compounds are described.