Electric Literature of 1594-57-6 ,Some common heterocyclic compound, 1594-57-6, molecular formula is C6H7N3O, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
To a solution of 4- (Boc-aminomethyl)-benzoic acid (187 mg) in DMF (0.25 M) were added DIEA (5 eq), TBTU (1 eq) and HOBt (0.2 eq). The solution was stirred at RT for 3 minutes, and then isonicotinamide oxime (102mg, 1 eq) was added. After 1 hour, the solvent was evaporated. The residue was triturated with 0.05 M NaOH (5 ml). The solid was filtered off, washed with water and dried under vacuum. The solid was dissolved in DMF (0.25 M). The reaction mixture was heated at 110C for 2 hours. The reaction mixture was cooled down at RT. The precipitate was filtered off, washed with water, and then dried under vacuum. The solid was dissolved in 3N HCI. The solution was heated at 50C for 2 hours. The solvent was evaporated and the residue was dried under vacuum. The title product was obtained as a white powder (74% yield).’H NMR (300 MHz, DMSO-d6): 4.15 ppm (q, 2H, J=5.7 Hz); 5.00 ppm (bs, 2H); 7.80 ppm (d, 2H, J=8.4 Hz); 8.24 ppm (m, 4H); 8.95 ppm (d, 2H, J=6.0 Hz).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1594-57-6, N-Hydroxyisonicotinimidamide, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; DEVGEN NV; WO2005/82367; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem