Trimethylacetamide → HCID 90403369, compound

Participants

Reaction Steps

A solution of 2,2,2-trimethylacetamide (0.040 g, 0.400 mmol) in DCE (2 mL) was treated with oxalyl chloride (0.035 mL, 0.400 mmol), stirred at RT for 5 min, then warmed to 80° C. for 0.5 h. The solution was cooled to RT, added to a mixture of 6-methyl-5-((2-(4-(4-methylpiperazin-1-yl)phenyl)pyridin-4-yl)oxy)pyridin-2-amine (0.10 g, 0.266 mmol) and DIEA (0.2 mL, 1.145 mmol) in dioxane (4 mL) and stirred at RT for 3 h. The mixture was treated with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were washed with 1N NaOH, then brine, dried over Na2SO4 and concentrated to dryness. The material was treated with MeCN, and the resulting solid was collected via filtration and dried to afford N-((6-methyl-5-((2-(4-(4-methylpiperazin-1-yl)phenyl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamide (75 mg, 56%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.16 (br s, 1H), 10.40 (br s, 1H), 8.43 (d, J=5.6 Hz, 1H), 7.94-7.87 (m, 3H), 7.65 (d, J=8.8 Hz, 1H), 7.33 (d, J=2.4 Hz, 1H), 6.97 (d, J=8.8 Hz, 2H), 6.65 (dd, J=5.6, 2.4 Hz, 1H), 3.21 (t, J=4.6 Hz, 4H), 2.44 (br s, 4H), 2.27 (s, 3H), 2.21 (s, 3H), 1.21 (s, 9H); MS (ESI) m/z: 503.3 (M+H+).

Provenance & Evidence