Pyridine → HCID 86274904, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2,2,2-trimethylacetamide (0.297 g, 2.94 mmol) in DCE (5 mL) was treated with oxalyl chloride (0.236 mL, 2.79 mmol), heated at 100° C. for 1 h, cooled to RT, added drop-wise to a solution of N-(4-((6-amino-2-methylpyridin-3-yl)oxy)pyridin-2-yl)pyrrolidine-1-carboxamide (0.658 g, 2.100 mmol) and pyridine (0.237 mL, 2.94 mmol) in THF (10 mL) and stirred at RT for 2 h. The mixture was concentrated to dryness, treated with satd. NaHCO3, extracted with EtOAc (4×) and the combined organics were dried over Na2SO4 and concentrated to dryness. The residue was treated with MeCN, sonicated and the resulting solid was removed via filtration. The filtrate was concentrated to dryness, suspended in MeCN, sonicated, allowed to stand for 3 h and the resulting solid collected via filtration to afford N-(4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)pyrrolidine-1-carboxamide (161 mg, 17%). 1H NMR (400 MHz, DMSO-d6): δ 11.16 (s, 1H), 10.41 (s, 1H), 8.70 (s, 1H), 8.09 (d, J=5.7 Hz, 1H), 7.90 (m, 1H), 7.61 (d, J=8.8 Hz, 1H), 7.38-7.37 (m, 1H), 6.55 (dd, J=5.7, 2.4 Hz, 1H), 3.31 (m, 4H), 2.23 (s, 3H), 1.78 (m, 4H), 1.21 (s, 9H); MS (ESI) m/z: 441.2 (M+H+).

Provenance & Evidence