Acetic Acid → HCID 178525786, compound

Participants

Reaction Conditions

Reaction Steps

(R)-1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylic acid, prepared during the previous step, was dissolved in a mixture of N,N-dimethylformamide (45.5 mL) and water (4.9 mL). Ammonium formate (1.925 g, 30.625 mmol) was added followed by zinc dust (1.05 g, 15.3 mmol). The reaction mixture was stirred at 45° C. for 16 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. To the residue was added N,N-dimethylformamide (24.5 mL) followed by a solution of 2-cyclopropylpyrimidine-4-carbaldehyde in N,N-dimethylformamide (24.5 mL, 6.125 mmol, 0.25M) and acetic acid (3.675 mL, 61.25 mmol). The reaction mixture was stirred at 60° C. for 16 h. The solvent was removed under reduced pressure and the residue was purified via preparative HPLC to afford the title compound (0.637 g, 28.6%).

Provenance & Evidence