Sodium Azide → 6-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carbonyl azide

Participants

Reaction Steps

To a stirred solution of 6-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carboxylic acid 13B (3.6 g, 9.65 mmol), N-ethyl-N-isopropylpropan-2-amine (7.48 g, 57.9 mmol) and sodium azide (6.27 g, 96 mmol) in anhydrous DMF (60 mL), PyBOP (6.02 g, 11.58 mmol) was added in portions at ambient temperature over 5 min. The reaction was stirred for another 30 min and then poured into a EtOAc/H2O (100/300 mL) mixture and shaken well. The resulting precipitate was filtered, rinsed with H2O followed by EtOAc, and dried in vacuum over P2O5 for 18 hrs to provide the title compound, 6-((6-bromo-1H-benzo[d][1,2,3]triazol-1-yl)methyl)imidazo[1,2-b]pyridazine-2-carbonyl azide 13C (2.1 g, 5.28 mmol, 55%). The EtOAc solution washed with 5% citric acid (2×100 mL), NaHCO3, dried with MgSO4, filtered and concentrated to dryness to give additional crude product (1.6 g of 80% pure material). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.28 (s, 2 H) 7.37 (d, J=9.60 Hz, 1 H) 7.59 (dd, J=8.84, 1.77 Hz, 1 H) 8.09 (d, J=8.84 Hz, 1 H) 8.26 (d, J=10.10 Hz, 1 H) 8.32 (d, J=1.26 Hz, 1 H) 8.92 (s, 1H). MS:m/z 398.2 (M+H)+.

Provenance & Evidence