Trimethylacetamide → HCID 86274907, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2,2,2-trimethylacetamide (0.150 g, 1.480 mmol) in DCE (4 mL) was treated with oxalyl chloride (0.130 mL, 1.480 mmol), heated at 80° C. for 1 h, cooled to RT, added drop-wise to a solution of 4-((6-aminopyridin-3-yl)oxy)-N-cyclopropylpicolinamide (0.2 g, 0.740 mmol) and DIEA (0.646 mL, 3.70 mmol) in dioxane (4 mL) and stirred at RT for 20 h. The mixture was diluted with EtOAc, washed with satd. NaHCO3, water, then brine and the combined aqueous washes were back-extracted with EtOAc. The combined organics were dried over Na2SO4, concentrated to dryness and purified by silica gel chromatography (EtOAc/DCM) to afford N-cyclopropyl-4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)picolinamide (0.196 g, 67%). 1H NMR (400 MHz, DMSO-d6): δ 11.24 (s, 1H), 10.46 (s, 1H), 8.75 (d, J=5.1 Hz, 1H), 8.50 (d, J=5.6 Hz, 1H), 8.30 (d, J=2.9 Hz, 1H), 8.11 (d, J=9.0 Hz, 1H), 7.78 (dd, J=9.0, 2.9 Hz, 1H), 7.40 (d, J=2.6 Hz, 1H), 7.19 (dd, J=5.6, 2.6 Hz, 1H), 2.87-2.85 (m, 1H), 1.21 (s, 9H), 0.65 (d, J=8.0 Hz, 4H); MS (ESI) m/z: 398.2 (M+H+).

Provenance & Evidence