Application of 68282-53-1, A common heterocyclic compound, 68282-53-1, name is 5-Methyl-1H-imidazole-4-carbaldehyde, molecular formula is C5H6N2O, its 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 12.1. 31: 4-({6,7-DIMETHOXY-2-[(4-METHYL-1H-IMIDAZOL-5- YL)METHYL]-1,2,3,4-TETRAHYDROISOQUINOLIN-1-YL}METHOXY)-N,N- DIETHYLBENZAMIDE; To a solution of INTERMEDIATE 5. 1. 1 (0.2 mg, 0.5 mmole) and 4-methyl-5- imidazolecarboxaldehyde (0.06 g, 0.6 mmole) in 1,2-dichloromethane (5 mL) was added sodium triacetoxyborohydriden (0.32 g, 1.5 mmole) and the resulting solution was stirred at room temperature for 18 h. Sodium hydroxide (1M, 20 mL) and chloroform (60 mL) was added and the mixture filtered through a Whatman IPS filter paper. The solvent was removed from the organic phase in vacuo and the residue purified by flash chromatography (2/98 Methanol/Chloroform) to give COMPOUND 12.1. 31 (0.06 g, 25%) as a yellow amorphous solid. 1H NMR (500 MHz, CDC13) : No. 1.17 (br s, 6 H), 2.14 (s, 3H), 2.56 (dd, J4,14. 5 Hz, 1H), 3.83 (m, 2H), 3.84 (s, 3H), 3.86 (s, 3H), 4.03 (app q, J 5 Hz, 2H), 4.27 (app t, J 10 Hz, 1H), 5.95 (br s, 1H), 6.62 (s, 1H), 6.67 (s, 1H), 6.87 (d, J 9 Hz, 2H), 7.31 (d, J9 Hz, 2H), 7.49 (s, 1H). 13C NMR (125 MHz, CDC13) : i5ll. 28,24. 22,44. 38,48. 34,55. 86,56. 01,59. 20,71. 59, 111. 14, 111. 56, 114. 30, 125.38, 125.64, 127.12, 128. 18, 129.78, 130.76, 132.99, 147.53, 148. 17,159. 27,171. 15. (+) LRESIMS mlz 493 [M+H] +.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; ASTRAZENECA AB; WO2005/61484; (2005); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem