1-Hydroxybenzotriazole → HCID 59233248, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of lithium 2-(6-chloropyridazin-3-yl)propanoate (7.2 g, 37.4 mmol), 5-bromo-2-hydrazinylpyridine (7.03 g, 37.4 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (5.05 g, 37.4 mmol), and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (7.89 g, 41.1 mmol) in DMF (Volume: 320 ml) was stirred for 4 hrs at 25° C. The reaction was poured into H2O (2 L) and extracted with EtOAc (3×500 mL). The organic phase was dried over MgSO4, filtered, and evaporated to dryness. The resulting residue was purified by MPLC CHCl3:MeOH (9:1) to provide the title compound, N′-(5-bromopyridin-2-yl)-2-(6-chloropyridazin-3-yl)propanehydrazide 48C (5.5 g, 15.42 mmol, 41.2% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.52 (d, J=7.33 Hz, 3 H) 4.17 (d, J=7.07 Hz, 1 H) 6.52 (d, J=8.84 Hz, 1 H) 7.67 (dd, J=8.84, 2.53 Hz, 1 H) 7.87 (d, J=9.09 Hz, 1 H) 7.94 (d, J=8.84 Hz, 1 H) 8.11 (d, J=1.77 Hz, 1 H) 8.66 (d, J=1.52 Hz, 1 H) 10.20 (d, J=1.52 Hz, 1 H). ESI-MS:m/z 356.1 (M+H)+.

Provenance & Evidence