Trimethylacetamide → N-(4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide

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Reaction Steps

A solution of 2,2,2-trimethylacetamide (0.046 g, 0.457 mmol) in DCE (2 mL) was treated with oxalyl chloride (0.040 mL, 0.457 mmol), stirred at RT for 0.5 h, then heated at 75° C. for 1 h. The mixture was cooled to RT, treated with a solution of Example A5 (0.10 g, 0.352 mmol) and TEA (0.098 mL, 0.703 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-(4-((2-methyl-6-(3-pivaloylureido)pyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (57 mg, 39%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.16 (s, 1H), 10.86 (s, 1H), 10.41 (br s, 1H), 8.19 (d, J=5.6 Hz, 1H), 7.90 (m, 1H), 7.62 (d, J=8.9 Hz, 1H), 7.55 (m, 1H), 6.66 (m, 1H), 2.22 (s, 3H), 1.95 (m, 1H), 1.21 (s, 9H), 0.75 (d, J=5.9 Hz, 4H); MS (ESI) m/z: 412.2 (M+H+).

Provenance & Evidence