Category: 185961-99-3

Analyzing the synthesis route of 185961-99-3

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.

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
Piperidine | C5H11N – PubChem

 

Analyzing the synthesis route of 185961-99-3

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.

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.

Example 25; 1-(1 -{[5-(2-Chlorophenyl)-4-ethyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl]acetyl}-4- piperidinyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (E25)[5-(2-Chlorophenyl)-4-ethyl-7H-pyrrolo[2,3-d]pyrimidin-7-yl]acetic acid lithium salt (D27, 52.0 mg, 0.161 mmol) was dissolved in N,N-dimethylformamide (2 ml.) and N- methylmorpholine (0.035 mL, 0.322 mmol) added followed by 1- hydroxybenzotriazole (27.1 mg, 0.177 mmol) and 1-(3-dimethylaminopropyl)-3- ethylcarbodiimide hydrochloride (37.0 mg, 0.193 mmol). The mixture was stirred at room temperature under argon for 5 minutes then 1-(4-piperidinyl)-1 ,3-dihydro-2H- imidazo[4,5-b]pyridin-2-one (52.7 mg, 0.242 mmol) added. The reaction was stirred for 17 hours, then at 5O0C for 10 hours, concentrated under reduced pressure then partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried and concentrated under reduced pressure. The residue was purified by column chromatography, eluting with 0-5% 2M ammonia/methanol in dichloromethane to give a white solid. Further purification by MDAP gave the title compound as a white solid.LC/MS (ES+ve): [M+H]+ at m/z 516, 518 (C27H26CIN7O2 requires [M+H]+ at m/z 516,518).1H NMR delta (DMSOd6): 1.04 (3H, t), 1.74-1.92 (2H, m), 2.05-2.19 (1 H, m), 2.31-2.43(2H, m), 2.57-2.66 (2H, m), 2.74-2.85 (1 H, m), 4.22 (1 H, d), 4.43-4.57 (2H, m), 5.35 (2H, q), 6.98-7.04 (1 H, m), 7.45-7.52 (3H, m), 7.55 (1 H, s), 7.58-7.65 (2H, m), 7.90- 7.94 (1 H, m), 8.73 (1 H, s), 1 1.33-1 1.72 (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.

Reference£º
Patent; GLAXO GROUP LIMITED; WO2009/80682; (2009); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem