Dimethylformamide → HCID 86662435, compound

Participants

Reaction Steps

To a solution of 3,6-dichloropyridazinecarboxylic acid (1-1, 2.0 g, 10.4 mmol, 1.0 equiv) in dichloromethane (26 mL) was added catalytic DMF (0.16 mL, 2.1 mmol, 0.2 equiv) and oxalyl chloride (1.81 mL, 20.7 mmol, 2.0 equiv) at 0° C. The reaction mixture was stirred for 1 hour and concentrated. The crude residue was dissolved in dichloromethane (26 mL) and to the reaction was added 3,4-dimethoxybenzylamine (3.12 mL, 20.7 mmol, 2.0 equiv), TEA (1.81 mL, 20.8 mmol, 2.0 equiv), and DMAP (1.81 mL, 20.8 mmol, 2.0 equiv) at 0° C. The reaction mixture became cloudy with precipitate and was stirred 24 hours at ambient temperature. The reaction was partitioned between EtOAc and saturated NaHCO3. The organic phase was washed with NaHCO3, water and brine and dried over MgSO4. After concentration, the residue was purified by normal phase column chromatography (5 to 85% EtOAc in hexanes) to afford the product (1-2) as a yellow solid. ESI+MS [M+H]+ C14H13Cl2N3O3: 342.1 found, 342.0 required.

Provenance & Evidence