Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 66358-23-4, name is Imidazo[1,2-a]pyridin-5-amine. A new synthetic method of this compound is introduced below., Application In Synthesis of Imidazo[1,2-a]pyridin-5-amine
Example 69: 4-[3-(4-Chloro-phenoxy)-benzyl1-piperazine-1 -carboxylic acid imidazo[1 ,2-aipyridin-5-ylamide.; To a solution of imidazo[1 ,2-a]pyridin-5-ylamine (56.0 mg, 0.421 mmol) in CH2CI2 (2.0 ml_) were added N,N’-disuccinimidyl carbonate (108 mg, 0.421 mmol) and DMAP (51.0 mg, 0.417 mmol). The reaction mixture was stirred at rt for 6 h, then treated with 1-[3-(4-chloro-phenoxy)-benzyl]-piperazine hydrochloride (158 mg, 0.420 mmol) and diisopropylethylamine (109 mg, 0.840 mmol) and stirred for an additional 16 h at rt. The reaction mixture was diluted with EtOAc and extracted with H2O then saturated aqueous NaCI. The organic layer was dried (MgSO4), and concentrated. The crude residue was purified (FCC, 2 N NH3 in MeOH/DCM) to give 4-[3-(4-chloro- phenoxy)-benzyl]-piperazine-1 -carboxylic acid imidazo[1 ,2-a]pyridin-5-ylamide (90.0 mg, 46%). MS (ESI+): calcd for C25H24CIN5O2 m/z 461.17, found 462.2 (M+H)+. 1H NMR (d6-DMSO): 9.21 (br s, 1 H), 7.57 (s, 1 H), 7.54 (d, J = 1.2, 1 H), 7.47-7.35 (m, 4H), 7.23 (dd, J = 9.0, 7.2, 1 H), 7.15 (d, J = 7.6, 1 H), 7.06-7.01 (m, 3H), 6.94 (dd, J = 8.1 , 1.9, 1 H), 6.73 (d, J = 7.1 , 1 H), 3.54 (s, 2H), 3.52-3.45 (m, 4H), 2.46-2.40 (m, 4H).
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Reference:
Patent; JANSSEN PHARMACEUTICA NV; BREITENBUCHER, J., Guy; KEITH, John, M.; TICHENOR, Mark, S.; CHAMBERS, Alison, L.; JONES, William, M.; HAWRYLUK, Natalie, A.; TIMMONS, Amy, K.; MERIT, Jeffrey, E.; SEIERSTAD, Mark, J.; WO2010/68453; (2010); A1;,
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