New learning discoveries about 28697-07-6

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.28697-07-6,N-Cbz-2-Piperidinecarboxylic acid,as a common compound, the synthetic route is as follows.

Example 27N-(3,5-Dichloroisonicotinoyl)-4-(2-piperidin-2-yl-3H-imidazo[4,5-b]pyridin-3-yl)-L- phenylalanine (Compound 11) To Intermediate 2 (3.41g) in DCM (40ml) is added 1-Cbz-2-piperidinecarboxylic acid (4.48g), HOBt (346mg) and EDC (4.88g). The reaction is stirred at room temperature for 3 days. The reaction is partitioned between DCM (40ml) and water (40ml) and the organic layer washed with 10% AcOH solution (40ml). The solvent is removed in vacuo and the residue dissolved in AcOH (12ml) and heated in a microwave at 1200C for 10 minutes. The mixture is evaporated to dryness in vacuo and partitioned between EtOAc (40ml) and saturated NaHCO3 (40ml), the organic layer is dried over Na2SO4, filtered, evaporated to dryness and the residue purified by chromatography on silica eluting with EtOAc/heptane. To a portion of the purified material (1.25g) in DCM (20ml) is added TFA (1.51 ml) at room temperature. The reaction is stirred at room temperature for 20 hours. The reaction is partitioned between DCM (50ml) and saturated NaHCO3 (50ml), dried over Na2SO4, filtered and the evaporated to dryness. To a portion of the obtained material (348mg) in DCM (4ml) is added DIPEA (138mul) followed by 2,6-dichloroisonicotinoyl chloride (169mg) in DCM (2ml). The reaction is stirred at room temperature for 1 hour. The reaction is partitioned between DCM (40ml) and water (40ml). The organic layer is dried over Na2SO4, filtered and evaporated to dryness in vacuo and the residue purified by chromatography on silica eluting with EtOAc/heptane. To the purified material (310mg) in EtOH (10ml) under N2(g) is added 10% Pd on carbon (50mg). The mixture is flushed with H2(g) and stirred at atmospheric pressure for 3 days. The mixture is filtered through a pad of celite, and the filtrate evaporated to dryness in vacuo. The crude material is dissolved in THF (4ml) and added slowly over 1 hour to a stirred solution of NaOH (2.0M, 5ml). Once addition is complete the reaction is stirred at room temperature for 1 hour, the reaction mixture acidified to acidic pH with HCI (6.0M), concentrated in vacuo and purified by preparative HPLC (Method C) to afford the title compound as a white solid (61 mg, 1%). LCMS (Method A) 539 [M+H] RT 1.72 mins. 1H NMR 300MHz (CDCI3) .81.10-1.41 (m, 2H), 1.43-1.60 (m, 2H), 1.70 (m, 2H), 1.88 (d, 1 H), 2.41 (m, 1 H), 3.00 (m, 2H), 3.39 (d, 1 H), 3.75 (d, 1 H), 4.77 (m, 1 H), 7.25 (m, 3H), 7.50 (d, 2H), 8.00 (d, 1 H), 8.09 (dd, 1 H), 8.40 (s, 2H), 28697-07-6

The synthetic route of 28697-07-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; UCB PHARMA, S.A.; WO2008/64823; (2008); A1;,
Piperidine – Wikipedia
Piperidine | C5H11N – PubChem