Trimethylacetamide → N-((6-methyl-5-((2-propionamidopyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamide

Participants

Reaction Steps

A solution of 2,2,2-trimethylacetamide (0.048 g, 0.477 mmol) in DCE (2 mL) was treated with oxalyl chloride (0.042 mL, 0.477 mmol), stirred at RT for 0.5 h, then heated at 75° C. for 1 h. The mixture was cooled to RT, added to a solution of Example A6 (0.10 g, 0.367 mmol) and TEA (0.1 mL, 0.744 mmol) in THF (2 mL) and stirred at RT for 1 h. The mixture was concentrated to dryness, the residue treated with EtOAc, the solid collected via filtration, washed with water and EtOAc and dried to afford N-((6-methyl-5-((2-propionamidopyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamide (87 mg, 59%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.17 (s, 1H), 10.49 (s, 1H), 10.41 (br s, 1H), 8.17 (d, J=5.7 Hz, 1H), 7.90 (m, 1H), 7.63 (d, J=8.8 Hz, 1H), 7.59 (d, J=2.4 Hz, 1H), 6.65 (dd, J=5.7, 2.4 Hz, 1H), 2.33 (q, J=7.5 Hz, 2H), 2.23 (s, 3H), 1.22 (s, 9H), 0.99 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 400.2 (M+H+).

Provenance & Evidence