Formaldehyde → HCID 73330788, compound

Participants

Reaction Steps

To a solution of 4-(4-((1-methyl-3-(3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,4-triazol-5-yl)methyl)pyridin-2-yl)piperazin-1-ium formate (100 mg, 0.2 mmol) in EtOH (1 mL), formaldehyde (0.5 mL, 6.0 mmol, 38% in H2O) and paraformaldehyde (100 mg, 3.3 mmol) in EtOH (1 mL) was stirred at RT, then treated with NaBH3CN (63 mg, 1.0 mmol) in one portion. The mixture was stirred at RT for 1 h, and then concentrated to give the crude product, which was purified by pre-HPLC (Mobile phase: A=10 mM NH4HCO3/H2O, B=MeCN; Gradient: B=60%-95% in 18 min; Column: XBridge (C18, 5 um, 30 mm*150 mm) to afford 5-(1-methyl-5-((2-(4-methyl piperazin-1-yl)pyridin-4-yl)methyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole as a white solid (50 mg, 50%). MS (ES+) C23H23F3N8O2 requires: 500, found: 501[M+H]+; 1H NMR (500 MHz, DMSO-d6) δ ppm 8.28 (bs, 1H), 8.22 (d, J=7.0 Hz, 2H), 8.05 (d, J=5.0 Hz, 1H), 7.60 (d, J=8.0 Hz, 2H), 6.80 (s, 1H), 6.55 (d, J=5.0 Hz, 1H), 4.25 (s, 2H), 4.00 (s, 3H), 3.47 (t, J=4.8 Hz, 4H), 2.50 (t, J=5.3 Hz, 4H), 2.21 (s, 3H).

Provenance & Evidence