17228-38-5

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
1H-Benzimidazol-2-amine,N-methyl-(9CI) is utilized as a chemical intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and properties make it a valuable component in the development of new drugs for the treatment of different diseases.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1H-Benzimidazol-2-amine,N-methyl-(9CI) is employed as a building block for the design and synthesis of novel bioactive molecules. Its chemical versatility allows for the creation of diverse chemical entities with potential therapeutic applications.
Potential Applications in Disease Treatment:
Although specific details about the biological activities and safety profile of 1H-Benzimidazol-2-amine,N-methyl-(9CI) require further investigation, its potential applications in the treatment of various diseases make it a subject of interest for researchers. Its unique chemical structure may contribute to the development of new therapeutic agents with improved efficacy and safety profiles.

Upstream product

• 122128-69-2 1-benzylideneamino-2-methylaminobenzimidazole 
• 122128-70-5 2-methylamino-1-(p-nitrobenzylidene)aminobenzimidazole 
• 107879-46-9 1-Amino-2-methylaminobenzimidazole 
• 471-29-4 1-methylguanidine 
• 615-42-9 1,2-Diiodobenzene 
• 934-32-7 1H-benzimidazol-2-amine 
• 78508-34-6 2-(p-tolylthiomethylamino)benzimidazole 
• 4857-06-1 2-chloro-1H-benzoimidazole 
• 74-89-5 methylamine 

Relevant academic research and scientific papers

Nucleophilic aromatic substitution of heterocycles using a high-temperature and high-pressure flow reactor

We report herein a high-temperature and high-pressure continuous-flow protocol to carry out nucleophilic aromatic substitution (SNAr) of heterocycles with nitrogen nucleophiles. Utilizing the Phoenix Flow Reactor in parallel with Design-of-Experiment software enabled rapid optimization of the SNAr protocol. This protocol facilitated efficient synthesis of a broad range of 2-aminoquinazolines, and was extended to 2-aminoquinoxalines and 2-aminobenzimidazoles.

Catalyst-controlled chemoselective arylation of 2-aminobenzimidazoles

What N would you like? The chemoselective and complementary Pd- and Cu-catalyzed N-arylation of 2-aminobenzimidazoles is described. Selective N-arylation of the amino group was achieved with a Pd-catalyzed method, while selective N-arylation of azole nitrogen was achieved with a Cu-catalyzed procedure (see scheme). Copyright

CHEMICAL COMPOUNDS

There is provided pyrimidinyl compounds of Formula (I), wherein: R2 is or pharmaceutically acceptable salts thereof, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

CuI-catalyzed amination of arylhalides with guanidines or amidines: A facile synthesis of 1-H-2-substituted benzimidazoles

(Figure Presented) CuI/L5 (N,N′-dimethylethylenediamine) proves to be an efficient catalyst system for the amination of arylhalides with guanidines. The same catalyst system is then successfully applied to the one-step synthesis of 1-H-2-aminobenzimidazol

OXIDATIVE CYCLIZATION OF 2-AMINO-1-ARYLIDENEAMINOBENZIMIDAZOLES INTO 1,2,4-TRIAZOLOBENZIMIDAZOLES

When heated in nitrobenzene, 1-arylideneamino-2-methylaminobenzimidazoles convert in a 20...30percent yield into 2-aryl-3-methyl-1,2,4-triazolobenzimidazoles.In addition, 2-methylaminobenzimidazole and the corresponding benzonitrile are formed as a result of thermal splitting of the N-N bond.Under the same conditions, 2-amino-1-arylideneaminobenzimidazoles and 1-arylideneamino-3-methylbenzimidazoline-2-imines give only products of splitting off of the nitrile.In several cases, the subsequent reaction of the nitrile with 2-amino-1-methylbenzimidazole leads to the formation of benzamidines.

Conformational Properties of the Free and Methylated 2-Amino Group in Benzimidazole, Benzoxazole, and Benzothiazole. X-Ray Crystallographic Analysis and Nuclear Magnetic Resonance Study of the Internal Rotation

The conformational properties of the free and methylated 2-amino group in benzimidazole, 1-methylbenzimidazole, benzo-oxazole, and benzothiazole were studied, as well as the modifications induced by N-protonation and N-methylation at the heterocyclic ring.Both 1H n.m.r. spectra and X-ray analysis show that in the ground state of the molecules examined the amino group is coplanar with respect to the plane of the rings.The NN-dimethylamino group tends to be distorted from coplanarity when a methyl group is present at the heterocyclic nitrogen: the degree of distortion determined experimentally compares satisfactorily with that corresponding to the energy minimum of the molecules calculated by semi-empirical methods.For the benzoxazole and benzothiazole derivatives it was also possible through 1H dynamic n.m.r. measurements to determine the thermodynamic parameters for the internal rotation of the NN-dimethylamino group; and in the N-protonated forms the free energy of activation turns out to be higher than that in the free bases.

Sodium Borohydride Reduction of Adducts of Primary Amines with Aldehydes and p-Thiocresol. The Alkylation of Heterocyclic and Aromatic Amino-compounds

p-Nitroaniline, 2-aminopyridine (1a), 4-aminopyridine (2a), 2-amino-4-methylpyrimidine (8a), 2-aminothiazole (10a), and 2-aminobenzimidazole (12a) react with aqueous formaldehyde and p-thiocresol in ethanol or methanol solution to give N-(p-tolylthiomethyl) derivatives , usually in high yields.When the latter compounds are heated, under reflux, with an excess of sodium borohydride in ethanol or 1,2-dimethoxyethane solution, the corresponding methylamino-compounds are obtained.By a similar two-step prosedure in which aqueous formaldehyde is replaced, as appropriate, by anhydrous acetaldehyde, propionaldehyde, or benzaldehyde, p-nitroaniline is converted into N-ethyl-p-nitroaniline, p-chloroaniline is converted into p-chloro-N-(n-propyl)aniline, (1a) is converted into the corresponding ethylamino- and benzylamino-compounds (1c) and (1d), respectively, and (10a) and (12a) are converted into their 2-N-(n-propyl) derivatives (10c) and (12c), respectively.