2-chloro-N,N-dimethylacetamide → HCID 54762053, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of N-(4-(3-(5-tert-butylisoxazol-3-yl)ureido)phenyl)-5-(pyrrolidin-3-yloxy)picolinamide hydrochloride (150 mg, 0.30 mmol) in CH3CN (3 mL) was added TEA (126 μL, 0.90 mmol), KI (10 mg, 0.060 mmol), and 2-chloro-N,N-dimethylacetamide (21 μL, 0.30 mmol). The resulting mixture was heated at 85° C. for 1 h. LC-MS indicated that the reaction was complete. The reaction mixture was evaporated under reduced pressure and the residue was purified by reverse phase HPLC to give N-(4-(3-(5-tert-butylisoxazol-3-yl)ureido)phenyl)-5-(1-(2-(dimethylamino)-2-oxoethyl)pyrrolidin-3-yloxy)picolinamide (110 mg, 67%). LC-MS (ESI) m/z 550 (M+H)+.

Provenance & Evidence