Dimethylformamide → HCID 67290174, compound

Participants

Reaction Steps

To a solution of 4-(6-chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation B; 2.137 g, 5.701 mmol) in DCE (6 mL) and DMF (1 drop) was added oxalyl dichloride (0.5968 mL, 6.841 mmol), and the reaction was allowed to stir at ambient temperature for 1 hour. The evolution of gases slowed several times, and 3 more drops of DMF were added over the course of this activation step. Pyridine (24 mL) and 6-(4-(trifluoromethyl)phenyl)pyridazin-3-amine (1.5 g, 6.271 mmol) were added, and the reaction was heated to 80° C. overnight. The reaction mixture was diluted with EtOAc and washed with 10% citric acid, sodium bicarbonate and brine. The organic layer was dried over Na2SO4, filtered, and concentrated. The crude material was precipitated from EtOAc/hexanes to yield ethyl 7-chloro-6-(4-(6-(4-(trifluoromethyl)phenyl)pyridazin-3-ylcarbamoyl)phenoxy)-1,2,3,4-tetrahydronaphthalene-1-carboxylate (1.83 g, 3.070 mmol, 53.86% yield). MS (apci, positive) m/z=597.9.

Provenance & Evidence