Potassium Carbonate → HCID 86274187, compound

Participants

Reaction Steps

A suspension of 2-(dimethylamino)acetyl chloride hydrochloride (0.101 g, 0.638 mmol) in THF (5 mL) was added to a 0° C. solution of Example C1 (0.15 g, 0.455 mmol) and DIEA (0.239 mL, 1.366 mmol) in THF (5 mL), allowed to warm to RT and stirred overnight. Additional 2-(dimethylamino)acetyl chloride hydrochloride (0.200 g), DIEA (0.239 mL, 1.366 mmol) and DCM (5 mL) were added and the mixture stirred at RT overnight. The mixture was treated with 10% K2CO3, extracted with DCM (4×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via preparative TLC (MeOH/DCM/TEA) to afford N-((5-((2-(2-(dimethylamino)acetamido)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamide (86 mg, 46%). 1H NMR (400 MHz, DMSO-d6): δ 11.23 (s, 1H), 10.44 (s, 1H), 9.95 (s, 1H), 8.26 (d, J=2.9 Hz, 1H), 8.20 (d, J=5.8 Hz, 1H), 8.09 (d, J=9.0 Hz, 1H), 7.75 (dd, J=9.0, 2.9 Hz, 1H), 7.65 (d, J=2.4 Hz, 1H), 6.73 (dd, J=5.8, 2.4 Hz, 1H), 3.07 (s, 2H), 2.25 (s, 6H), 1.21 (s, 9H); MS (ESI) m/z: 415.2 (M+H+).

Provenance & Evidence