Reference of 124312-73-8,Some common heterocyclic compound, 124312-73-8, name is (1-Methyl-1H-imidazol-2-yl)methanamine, molecular formula is C5H9N3, 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 compound (225 mg) obtained in Example 55-3 was dissolved in methanol (4.0 ml). The solution was added with the compound (64.5 mg) obtained in Example 14-7 and trimethyl orthoformate (0.13 ml) and the whole was stirred at room temperature for 1.5 hours. After having been cooled to 0C, the reaction solution was added with sodium borohydride (20.8 mg) and the whole was stirred at room temperature for 20 minutes. After the reaction solution was concentrated under reduced pressure, the resultant residue was added with distilled water and the whole was subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with an anhydrous sodium sulfate. The drying agent was filtrated out and then the organic layer was concentrated under reduced pressure. The resultant was dissolved in methanol (6.0 ml). The reaction solution was added with 2-imidazole carboxaldehyde (83.3 mg) and sodium cyanoborohydride (77.3 mg). The whole was added with acetic acid to adjust the pH to 5 and stirred at room temperature for 18 hours. The reaction solution was concentrated under reduced pressure. The resultant residue was added with a 1 mol/l sodium hydroxide aqueous solution and the whole was subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution and dried with anhydrous sodium sulfate. The drying agent was filtrated out and then the organic layer was concentrated under reduced pressure. The resultant residue was purified through silica gel column chromatography (hexane/ethyl acetate) and treated with hydrochloric acid, thereby obtaining a hydrochloride (174.3 mg) of the subject compound as a white solid. MS(FAB,Pos.):m/z=567[M+H]+ 1H-NMR(500MHz,DMSO-d6):delta=0.90(6H,t,J=7.3Hz),1.64-1.86(8H,m),2.95(4H,br),3.05(2H,br),3.28(2H,br),3.67(3H,s),3.83(2H,s),4.10(2H,s),4.17(2H,s),5.94(2H,s),7.31-7.39(5H,m),7.49-7.54(3H,m),7.60(2H,s),7.72(1H,d,J=8.4Hz),8.17(1H,s),10.43(1H,br),14.94(2H,br).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (1-Methyl-1H-imidazol-2-yl)methanamine, its application will become more common.
Reference:
Patent; Kureha Corporation; EP1724263; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem