HCID 67198903, compound → HCID 67200218, compound

Participants

Reaction Steps

To a solution of amide 3 (3.46 g, 8.99 mmol) in MeOH (˜40 mL) was added a spatula tipful of 10% Pd/C, and the resulting suspension hydrogenated at 40 psi for 16 h. After this time, the reaction mixture was filtered through a pad of Celite, and solvent removed under reduced pressure. The residue was reprecipated from MeOH-EtOAc to give amine 4 as an amorphous cream solid (0.25 g, 15% from 1); mp 235-238° C. (powder -tar), 245-249° C. (gas evolved); 1H NMR: 13.85 (v br s, 1H, pyridine-N+—H), 10.75 (s, 1H, ArNHAr), 8.28 (d, J=7.23 Hz, 2H, ArH), 7.25 (s, 4H, ArH), 7.16 (d, J=8.44 Hz, 2H, ArH), 7.07 (d, J=7.03 Hz, 2H, ArH), 6.73 (d, J=7.79 Hz, 2H, ArH), 3.36 (s, ArC(O)N(CH3)Ar) [ArN+H3 not visible]; HRMS (EI) calc. for C19H18N4O m/z 318.1481, found 318.1481.

Provenance & Evidence