Triethylamine → 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-n-(6'-methoxy-3,5'-dimethyl-2,3'-bipyridin-6-yl)cyclopropanecarboxamide

Participants

Reaction Steps

To a solution of 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)cyclopropanecarboxylic acid (44.04 mg, 0.2 mmol) in dichloromethane (2 mL) was added thionyl chloride (14.6 μL, 0.20 mmol) followed by DMF (1 drop) and the reaction was stirred at room temperature for 30 minutes. The solvent was removed by rotovap. Toluene (˜1 mL) was added and mixed with the residue and then removed by rotovap. The toluene step was repeated once more and then the residue was placed under high vacuum for 10 minutes. It was then dissolved in dichloromethane (1 mL) and a solution of 6′-methoxy-3,5′-dimethyl-2,3′-bipyridin-6-amine (46 mg, 0.20 mmol) and triethylamine (83.6 μL, 0.60 mmol) in dichloromethane (1 mL) was added. The reaction was stirred at room temperature for 12 hours. The reaction was then concentrated. The residue was dissolved in DMSO and purified by reverse phase HPLC (10-99% CH3CN in water) to yield 16 mg of the product. ESI-MS m/z calc. 431.2. found 432.5 (M+1)+. Retention time 1.98 minutes.

Provenance & Evidence