With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.185961-99-3,1-(Piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one,as a common compound, the synthetic route is as follows.,185961-99-3
To a stirred solution of {5-[3-chloro-5-(4-methyl-1-piperazinyl)phenyl]-1 ,3,4-oxadiazol- 2-yl}acetic acid (obtainable by hydrolysis of D22, 0.15 g, 0.45 mmol) in N, N- dimethylformamide (5 mL) was added 1-(4-piperidinyl)-1 ,3-dihydro-2H-imidazo[4,5-b] pyridin-2-one (0.107 g, 0.49 mmol), O-(7-azabenzotriazol-1-yl)-lambda/,lambda/,lambda/’,/V- tetramethyluroniumhexafluorophosphate (0.19 g, 0.49 mmol) and N, N- diisopropylethylamine (0.086 mL, 0.49 mmol). The reaction mixture was stirred at room temperature under an atmosphere of argon for 3 hours. LC/MS showed acid starting material present and so further 1-(4-piperidinyl)-1 ,3-dihydro-2H-imidazo[4,5- b]pyridin-2-one (0.107 g, 0.49 mmol), O-(7-azabenzotriazol-1-yl)-lambda/,lambda/,lambda/’,/V- tetramethyluroniumhexafluorophosphate (0.19 g, 0.49 mmol) and N, N- diisopropylethylamine (0.086 mL, 0.49 mmol) were added and the reaction mixture was stirred overnight under an atmosphere of argon. The reaction mixture was concentrated under reduced pressure to give dark yellow oil. The crude product was purified by MDAP. The product containing fractions were combined and concentrated under reduced pressure to give a yellow oil. The title compound was transferred to a sample vial and dried at 40 0C under vacuum for 3 days. LC/MS (ES+ve): [M+H]+ at m/z 537, 539 (C26H29CIN8O3 requires [M+H]+ at m/z 537, 539).1H NMR delta (DMSO-de): 1.68-1.88 (2H, m), 2.04-2.17 (1 H, m), 2.22 (3H, s), 2.30-2.48 (5H, overlapping m), 2.72-2.82 (1 H, m), 3.20-3.40 (assumed 5H, overlapped by water signal, br m), 4.02-4.12 (1 H, m), 4.30-4.58 (4H, overlapping m), 6.90-6.99 (1 H, m), 7.20-7.25 (1 H, m), 7.30-7.33 (1 H, m), 7.38-7.40 (1 H, m), 7.57-7.62 (1 H, m), 7.87- 7.90 (1 H, m), 1 1.25 (1 H, br s).
185961-99-3 1-(Piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one 22293182, apiperidines compound, is more and more widely used in various fields.
Reference£º
Patent; GLAXO GROUP LIMITED; WO2009/819; (2008); A1;,
Piperidine – Wikipedia
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