6-Amino-3-chloropyridazine → HCID 86664394, compound

Participants

Reaction Steps

To a solution of 4-(6-chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation B; 0.500 g, 1.334 mmol) in 1,2-dichloroethane (1.3 ml) and DMF (1 drop) was added oxalyl chloride (0.1396 ml, 1.601 mmol), and the reaction was stirred for 1 hour at ambient temperature. The reaction was diluted with pyridine (5 ml) and 6-chloropyridazin-3-amine (0.2592 g, 2.001 mmol) was added. The reaction was heated to 80° C. for 16 hours, then diluted with EtOAc and washed with 1M hydrochloric acid, sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by silica gel chromatography eluting with a linear gradient of 5-70% EtOAc/hexanes to yield the desired compound (0.5 g, 1.028 mmol, 77.07% yield).

Provenance & Evidence