Synthetic Route of 68282-53-1,Some common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, 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.
COMPOUND 14. 1.2 : NnN-DIETHYL-4- {6-METHOXY-2-r (5-METHYL-1H- IMIDAZOL-4-YL . METHYL]-7-PHENOXY-1. 2e3. 4- TETRAHYDROISOQUINOLIN-1-YL} BENZAMIDE; To INTERMEDIATE 10.2. 1 (30 mg, 0.06 mmol) was added a solution of hydrochloric acid in 1,4-dioxane (4N, 0.5 mL) at room temperature. The reaction mixture was stirred for an hour then concentrated by a stream of nitrogen and dried under vacuum. The residue was re-dissolved in 1,2-dichloroethane (1.5 mL) and to this solution was added 4-methyl-lH-imidazole-5-carbaldehyde (-2eq, 0.12 mmol, 12 mg) and followed by sodium triacetoxyborohydride (4eq, 0.24 mmol, 50 mg). The reaction mixture was stirred for 20 hr then quenched with saturated aqueous sodium bicarbonate and extracted to dichloromethane (15 mL x 2). Excess aldehyde was removed by stirring the extracted dichloromethane with polymer supported hydrazine for 2 hr. The polymer was filtered off and the filtrate was concentrated and dried under vacuum. Product was purified by flash chromatography, using Si02 column with MeOH/DCM (10: 90) afford 17.9 mg (0.034 mmol, 60%) of COMPOUND 14. 1.2 as light yellow oil. 1H NMR (500 MHz, CDC13): b 1. 05 (br s, 3H), 1.18 (br s, 3H), 2.00 (s, 3H), 2.50-2. 98 (br m, 4H), 3.10 (br s, 2H), 3.28 (m ; 1H), 3.49 (br s, 2H), 3.52 (m, 1H), 3.72 (s, 3H), 4.45 (s, 1H), 6. 28 (s, 1H), 6.65 (s, 1H), 6.68-7. 20 (m, 9H), 7.26 (m, 1H). 13C NMR (125 MHz, CDC13) : 6 10.97, 13.09, 14.42, 28. 70,39. 65, 43. 68, 46.96, 49.24, 56.20, 67. 66,106. 00,112. 63,115. 47,116. 47,122. 02,126. 57, 129.91, 130.26, 131.76, 132.93, 136.34, 142. 69,145. 32, 150.37, 150.37, 171. 51. (+) LRESIMS m/z 525 (M+H) +.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Methyl-1H-imidazole-4-carbaldehyde, its application will become more common.
Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem