Nicotinic Acid → N-[3-(4-Cyclohexylcarbamoyl-piperidin-1-ylmethyl)-phenyl]-nicotinamide

Participants

Reaction Steps

To a solution of 1-(3-amino-benzyl)-piperidine-4-carboxylic acid cyclohexylamide BB-1 (200 mg, 0.57 mmol) in DCM (5 mL) are added successively nicotinic acid (70 mg, 0.57 mmol), HOBT (154 mg, 1.14 mmol), DMAP (14 mg, 0.11 mmol) and DIPEA (0.29 mL, 1.7 mmol). A solution of EDC hydrochloride (163 mg, 0.85 mmol) in DCM (2 mL) is added and the reaction mixture is stirred for 4 days at RT. The mixture is diluted with DCM (10 mL) and washed twice with sat.aq. NaHCO3 (20 mL). The combined organic phases are dried over MgSO4 and filtered. The solvent is evaporated under reduced pressure. The residue is dissolved in acetonitrile and purified by prep. HPLC E. LCMS C: tR=0.56 min; [M+H]+=421.4. 1H-NMR (DMSO-d6): δ 1.1-1.3 (m, 5H), 1.5-1.7 (m, 9H), 1.8-1.9 (m, 2H), 2.0-2.1 (m, 1H), 2.84 (d, J=9, 2H), 3.4-3.5 (m, 3H), 7.03 (d, J=7, 1H), 7.30 (t, J=7, 1H), 7.5-7.8 (m, 4H), 8.29 (d, J=8, 1H), 8.7-8.8 (m, 1H), 9.11 (s, 1H), 10.4 (s, 1H).

Provenance & Evidence