Acetic Acid → HCID 71522748, compound

Participants

Reaction Conditions

Reaction Steps

2-(Propan-2-yloxy)-6-(pyrrolidin-3-yl)pyridine a1-61 (0.302 g, 1.464 mmol, 1 eq) is dissolved in methanol (15 ml) and the solution is cooled at 0° C. Acetic acid (0.527 g, 8.784 mmol, 6 eq), N,N,-diisopropylethylamine (0.378 g, 2.928 mmol, 2 eq) and sodium cyanoborohydride (0.552 g, 8.784 mmol, 6 eq) are added. The reaction mixture is stirred for 5 min, and then poured on crude [2-(2-oxopiperidin-1-yl)pyridin-3-yl]acetaldehyde a4-3 (1.46 mmol, 1 eq) cooled at 0°. After 10 min at 0° C., the reaction mixture is warmed up to room temperature. Hydrochloric acid 1N is added until acidic pH. The solution is catched over an acidic column, washed with methanol and then released with ammonia 1M in methanol. The solvent is evaporated under reduced pressure. The residue is purified by LC-MS basic reverse phase (gradient CH3CN/H2O/NaHCO3 from 5/95/0.5 to 95/5/0.5). The residue of evaporation is dissolved in a minimum of acetone and oxalic acid (1 eq) is added to form the salt. The solvent is removed under reduced pressure. The residue is taken in diethyl ether, the mixture is stirred, sonicated and filtered. The precipitate is washed with diethyl ether (2 times) to afford 75 mg of 1-[3-(2-{3-[6-(propan-2-yloxy)pyridin-2-yl]pyrrolidin-1-yl}ethyl)pyridin-2-yl]piperidin-2-one oxalate 94.

Provenance & Evidence