Sodium Bicarbonate → 6-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)difluoromethyl)-N-(2,4-dimethoxybenzyl)pyridazin-3-amine

Participants

Reaction Conditions

Reaction Steps

A reaction mixture of 6-bromo-3-((6-chloropyridazin-3-yl)difluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine (0.5 g, 1.387 mmol), (2,4-dimethoxyphenyl)methanamine (0.696 g, 4.16 mmol) and NaHCO3 (0.58 g, 7.0 mmol) in IPA (10 mL) was heated at 140° C. in a microwave for 1 hr. The solvent was removed via rotary evaporation and the resulting residue was reconstituted in EtOAc. The organic solution was washed with water, separated and passed through a short silica plug to provide the title compound, 6-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)difluoromethyl)-N-(2,4-dimethoxybenzyl)pyridazin-3-amine 45G (0.6 g, 1.22 mmol, 88%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.71-3.76 (s, 3 H) 3.79 (s, 3 H) 3.85-3.89 (m, 2 H) 6.46 (dd, J=8.34, 2.53 Hz, 1 H) 6.57 (d, J=2.27 Hz, 1 H) 6.61-6.66 (m, 1 H) 7.08 (d, J=9.35 Hz, 1 H) 7.14 (d, J=8.34 Hz, 1 H) 7.81 (d, J=9.35 Hz, 1 H) 7.99 (dd, J=9.60, 1.01 Hz, 1 H) 8.70 (s, 1 H). ESI-MS:m/z 491.1 (M+H)+.

Provenance & Evidence