Trimethylacetamide → HCID 90403157, compound

Participants

Reaction Steps

A solution of 2,2,2-trimethylacetamide (0.084 g, 0.834 mmol) in DCE (3 mL) was treated with oxalyl chloride (0.073 mL, 0.834 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 6′-(bis(tert-butoxycarbonyl)amino)-4-((6-aminopyridin-3-yl)oxy)-[2,3′-bipyridine](0.2 g, 0.417 mmol) and TEA (0.174 mL, 1.251 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 and concentrated to dryness to afford N-((5-((6′-(bis(tert-butoxycarbonyl)amino)-[2,3′-bipyridin]-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamide (230 mg, 91%) as a white amorphous solid. 1H NMR (400 MHz, DMSO-d6): δ 11.22 (s, 1H), 10.45 (br s, 1H), 9.08 (d, J=2.5 Hz, 1H), 8.58 (d, J=5.7 Hz, 1H), 8.49 (dd, J=8.5, 2.5 Hz, 1H), 8.30 (d, J=2.9 Hz, 1H), 8.10 (d, J=9.0 Hz, 1H), 7.78 (dd, J=9.0, 2.9 Hz, 1H), 7.73 (d, J=2.4 Hz, 1H), 7.48 (d, J=8.4 Hz, 1H), 6.94 (dd, J=5.7, 2.4 Hz, 1H), 1.40 (s, 18H), 1.21 (s, 9H); MS (ESI) m/z: 607.3 (M+H+).

Provenance & Evidence