Trimethylacetamide → HCID 90403362, compound

Participants

Reaction Steps

A solution of 2,2,2-trimethylacetamide (0.062 g, 0.610 mmol) in DCE (3 mL) was treated with oxalyl chloride (0.080 mL, 0.915 mmol), stirred at RT for 1 h, then heated at 75° C. for 3 h. The mixture was cooled to RT, treated with a solution of tert-butyl (4-((6-aminopyridin-3-yl)oxy)-[2,3′-bipyridin]-6′-yl)(methyl)carbamate (0.12 g, 0.305 mmol) and TEA (0.170 mL, 1.220 mmol) in DCM (3 mL) and stirred at RT for 2 h. The mixture was treated with brine, extracted with DCM (2×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford tert-butyl methyl(4-((6-(3-pivaloylureido)pyridin-3-yl)oxy)-[2,3′-bipyridin]-6′-yl)carbamate (100 mg, 63%) as a white amorphous solid. 1H NMR (400 MHz, DMSO-d6): δ 11.23 (s, 1H), 10.44 (s, 1H), 9.02 (d, J=2.5 Hz, 1H), 8.55 (d, J=5.7 Hz, 1H), 8.37 (dd, J=8.8, 2.5 Hz, 1H), 8.30 (d, J=2.9 Hz, 1H), 8.10 (d, J=9.0 Hz, 1H), 7.77-7.76 (m, 2H), 7.65 (d, J=2.4 Hz, 1H), 6.89 (dd, J=5.7, 2.4 Hz, 1H), 3.33 (s, 3H), 1.47 (s, 9H), 1.21 (s, 9H); MS (ESI) m/z: 521.3 (M+H+).

Provenance & Evidence