Reference of 934-22-5,Some common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, molecular formula is C7H7N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
The respective 2-oxo benzoic acid (1 eq.) was dissolved in THF (5 ml in case of 1 mmol) and DCC (1 eq.) was added. After stirring at r.t. for 1 h, benzimidazol-5(6)-amine (1 eq.) was added and stirring at r.t. was continued for 24 h. The mixture was put into the fridge for 2 h and afterwards the precipitated solid was filtered off. The filtrate was concentrated in vacuo, re-dissolved in a mixture of AcOH and toluol (3 ml and 7 ml in case of 1 mmol batch) and refluxed over night. After cooling the solvents were evaporated. The resulting residue was dissolved in CH2Cl2 (10 ml in case of 1 mmol batch), cooled to 0 C. and treated with TFA (1 ml (4 ml) per mmol). After stirring at r.t. for 10 min, triethylsilane (2 eq. (4 eq.)) was added. The reaction was allowed to warm up to room temperature and stirred for 3 h. After that time, the mixture was quenched with saturated sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with EtOAc (3¡Á25 ml). The combined organic layers were dried over Na2SO4, concentrated in vacuo and the remaining residue was purified by flash-chromatography using silica gel and a CHCl3/MeOH gradient. Example 1262-(1H-benzo[d]imidazol-5-yl)-3-(4-biphenyl)isoindolin-1-oneThe compound was synthesized according to method 11.2-(4-Phenylbenzoyl)benzoic acid (1.0 g; 3.3 mmol), DCC (680 mg; 3.3 mmol), benzimidazol-5(6)-amine (440 mg; 3.3 mmol), TFA (3.92 ml) and triethylsilane (0.624 ml; 3.92 mmol; 4 eq.) and was additional purified by semi-preparative HPLC; yield: 0.120 g (9.1%); MS m/z: 402.1 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): delta 6.79 (s, 1H); 7.28-7.32 (m, 1H); 7.36-7.40 (m, 5H); 7.53-7.60 (m, 5H); 7.63-7.66 (m, 1H); 7.72-7.74 (d, 1H, 3J=8.7 Hz); 7.76-7.79 (dd, 1H, 4J=1.7 Hz, 3J=8.7 Hz); 7.89-7.91 (m, 1H); 8.17-8.18 (d, 1H, 4J=1.7 Hz); 9.06 (s, 1H); HPLC (Gradient 3): rt 15.20 min (97.0%)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Aminobenzimidazole, its application will become more common.
Reference:
Patent; PROBIODRUG AG; US2011/92501; (2011); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem