With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.139022-25-6, name is Imidazo[1,2-a]pyridine-6-carboxylic acid, molecular formula is C8H6N2O2, molecular weight is 162.15, as common compound, the synthetic route is as follows.Product Details of 139022-25-6
(5-(([2 ‘-Bipyridin]-3-yloxy)methyl)-4,5-dihydroisoxazol-3-yl)methanamine hydrochloride (±) (product of step-2, 0.320 g, 0.997 mmol) was reacted with imidazo[l,2- a]pyridine-6-carboxylic acid (0.193 g,1.197 mmol) in presence of BOP reagent (0.485 g, 1.096 mmol) and DIPEA (0.525 mL, 2.991 mmol ) in DMF (10 mL) at room temperature for 16 h. The reaction mixture was diluted with water (10 mL) extracted with ethyl acetate (50 mL) and washed with water (4 x 50 mL). The organic phase was dried over sodium sulphate and concentrated under reduced pressure to get a residue. The residue was purified by combiflash column chromatography (dichloromethane/methanol/triethylamine = 91/8/1) to afford the title compound (0.150 g, 35%) as a solid. LCMS: nt/z 428.7 [M+H] +; HPLC: 97.93 % ; NMR (400 MHz, DMSO-de): delta 9.16 – 9.12 (d, / = 1.8 Hz, 1H), 9.11 (s, 1H), 9.05 – 8.99 (t, / = 5.5, 5.5 Hz, 1H), 8.61 – 8.54 (dt, / = 3.3, 1.5, 1.5 Hz, 1H), 8.37 – 8.31 (d, / = 4.5 Hz, 1H), 8.30 – 8.25 (m, 1H), 8.11 (s, 1H), 7.68 – 7.60 (m, 4H), 7.51 – 7.45 (dd, / = 7.9, 4.8 Hz, 1H), 7.45 – 7.39 (dd, / = 8.4, 4.6 Hz, 1H), 5.01 – 4.91 (dq, / = 10.4, 5.6, 5.6, 5.4 Hz, 1H), 4.28 – 4.12 (m, 4H), 3.27 – 3.15 (dd, / = 17.6, 11.2 Hz, 1H), 3.00 – 2.86 (dd, / = 17.7, 7.1 Hz, 1H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,139022-25-6, Imidazo[1,2-a]pyridine-6-carboxylic acid, and friends who are interested can also refer to it.
Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; (74 pag.)WO2016/12958; (2016); A1;,
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