Reference of 2963-77-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2963-77-1, name is 4-(1H-Benzo[d]imidazol-2-yl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.
Oxalyl chloride (191 muL) was added to a solution of 1-methyl-1H-pyrazole-5-carboxylic acid (200 muL) in DCM (2 mL) and DMF (1 drop). After 1 hour, the reaction mixture was evaporated. A solution of 4-(1H-benzo[d]imidazol-2-yl)aniline (166 mg) and triethylamine (420 muL), in DCM (4 mL) was added to the initial reaction residue and stirred at ambient temp for 1 hour. The Reaction mixture was diluted with DCM and extracted sequentially with sat bicarb, water, brine, then dried over sodium sulfate, filtered and evaporated. The bis acylated material was purified on silica, eluting with a gradient of ethyl acetate (50-100%) in hexane. The pure bis acylated material was treated with ethylamine solution (2M in THF, 5 mL) for 18h. The reaction mixture was evaporated. Trituration with ethyl acetate / diethyl ether [1:4], afforded a solid which was collected by filtration (77mg, Y = 30%). UPLC-MS (Acidic Method, 4 min): rt 1.05 min, m/z 318.1 [M+H]+ 1H NMR (400 MHz, DMSO-d6) d ppm 12.83 (br s, 1H), 10.41 (s, 1H), 8.13-8.21 (m, 2H), 7.92 (d, J=8.8 Hz, 2H), 7.64 (br d, J=5.9 Hz, 1H), 7.56 (d, J=2.0 Hz, 1H), 7.52 (br d, J=6.4 Hz, 1H), 7.19 (br d, J=4.3 Hz, 2H), 7.11 (d, J=2.0 Hz, 1H), 4.11 (s, 3H).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(1H-Benzo[d]imidazol-2-yl)aniline, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; JAGUAHR THERAPEUTICS PTE LTD; METE, Antonio; HITCHIN, James, R.; GRAHAM, Mark; (46 pag.)WO2020/43880; (2020); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem