With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7689-62-5,2-Chloro-1,5-naphthyridine,as a common compound, the synthetic route is as follows.,7689-62-5
A glass microwave reaction vessel was charged with 1-(trans-3-aminocyclobutyl)-3-cyclopropyl-1H-imidazo[4,5-b]pyrazin-2(3H)-one hydrochloride (Intermediate 79, 0.133 g, 0.472 mmol), 2-chloro-1,5-naphthyridine (0.100 g, 0.608 mmol) and DMSO (2 mL). N,N-Diisopropylethylamine (0.250 mL, 1.437 mmol) was added and the reaction mixture was sealed under argon and heated at 100 C. for 59 h. The reaction was cooled to room temperature and partitioned between water/DCM. The aqueous layer was extracted with DCM (3*) and the combined organic layers were evaporated onto silica gel and purified by flash chromatography (Isco, (25 gram)) eluting with 2M NH3 in MeOH:CH2Cl2 (0:1?1:19) to give 67 mg (34%) of a white crystalline solid. ESI-MS 374.0 [M+1]. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.49 (dd, J=4.30, 1.56 Hz, 1H), 8.00 (d, J=3.33 Hz, 1H), 7.97 (d, J=3.33 Hz, 1H), 7.93 (d, J=9.19 Hz, 1H), 7.81-7.89 (m, 2H), 7.46 (dd, J=8.41, 4.11 Hz, 1H), 7.02 (d, J=9.19 Hz, 1H), 5.21 (m, 1H), 4.64-4.76 (m, 1H), 3.25-3.38 (m, 2H), 2.91-3.02 (m, 1H), 2.34-2.45 (m, 2H), 0.94-1.11 (m, 4H)
The synthetic route of 7689-62-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; AMGEN INC.; Allen, Jennifer R.; Amegadzie, Albert; Andrews, Kristin L.; Brown, James; Chen, Jian J.; Chen, Ning; Harrington, Essa Hu; Liu, Qingyian; Nguyen, Thomas T.; Pickrell, Alexander J.; Qian, Wenyuan; Rumfelt, Shannon; Rzasa, Robert M.; Yuan, Chester Chenguang; Zhong, Wenge; US2013/225552; (2013); A1;,
1,8-Naphthyridine – Wikipedia
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