Reference 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 12.1.55: N,N-DIETHYL-4-{7-[(4-METHYL-1H-IMIDAZOL-5- YL) METHYL1-6J. 8, 9-TETRAHYDROri31DIOXOLOr4, 5-F] ISOOUINOLIN-6- YL}BENZAMIDE; 4-Methyl-imidazole-5-carboxyaldehyde (76. 4 mg, 0.69 mmol) was added to a solution of INTERMEDIATE 5.1. 15 (122.6 mg, 0.35 mmol) in 1,2-dichloroethane (5 mL) and the reaction mixture stirred at room temperature for 10 min. Sodium triacetoxyborohydride (516 mg, 2.43 mmol) was added followed by N-methyl-2- pyrrolidinone (400 I1L) and the reaction mixture stirred at RT for 18 h. 1 N NaOH (5 mL) was added and the organic solvent removed in vacuo. The residue was extracted with EtOAc (3 x 20 mL) and the organic layer washed with water (20 mL). The organic layer was concentrated in vacuo and the residue purified by flash chromatography on Si02 column (EtOAc: MeOH 95: 5) to afford COMPOUND 12.1. 55 as an oil (35.6 mg, 23%). 1H NMR (500 MHz, CDC13) : 8 1.13 (br s, 3H), 1.25 (br s, 3H), 2.09 (s, 3H), 2.55 (m, 1H), 2. 78 (m, 1H), 3.09 (m, 1H), 3.28 (br s, 2H), 3.34-3. 40 (m, 2H), 3.55 (br s, 2H), 3.59 (d, J 13.5 Hz, 1H), 4. 58 (s, 1H), 5.96 (s, 1H), 6. 21 (d, J 8 Hz, 1H), 6.55 (d, J 8 Hz, 1H), 7.28-7. 32 (m, 4H), 7.36 (s, 1H) ; 13C NMR (125 MHz, CDCl3) : 8 11. 37, 13. 11, 14.42, 22.28, 39.61, 43.64, 45.72, 49.40, 67.41, 101. 30, 106.56, 117. 66,122. 17, 126.56, 129.73, 130.71, 131.73, 133.45, 136.22, 144.81, 145.28, 145.54, 171. 54; (+) LRESIMS m/z 447.20 [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