2-Methoxyethylamine → HCID 86275387, compound

Participants

Reaction Steps

A mixture of Example C2 (0.120 g, 0.290 mmol), 2-methoxyethylamine (0.1 mL, 1.15 mmol) and N-methylpyrrolidine (0.012 g, 0.145 mmol) in dioxane (5 mL) was heated at 80° C. overnight, cooled to RT, and concentrated to dryness. The residue was dissolved in DCM and stirred with sat'd NaHCO3. The aqueous layer was back-extracted with DCM (3×) and the organic phases combined, dried (Na2SO4) and concentrated to afford a light brown oil. The crude residue was purified via silica gel chromatography (MeOH/DCM) to afford a white solid, which was dissolved in MeCN/H2O, frozen and lypholized overnight to afford N-((5-((2-(3-(2-methoxyethyl)ureido)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)pivalamide as a white solid (54 mg, 43%). 1H NMR (400 MHz, DMSO-d6): δ 11.22 (s, 1H), 10.44 (s, 1H), 9.14 (s, 1H), 8.24 (d, J=2.9 Hz, 1H), 8.07-8.06 (m, 2H), 7.96 (s, 1H), 7.72 (dd, J=9.0, 2.9 Hz, 1H), 6.97 (d, J=2.3 Hz, 1H), 6.57 (dd, J=5.9, 2.4 Hz, 1H), 3.35-3.34 (m, 2H), 3.28-3.22 (m, 2H), 3.24 (s, 3H), 1.21 (s, 9H); MS (ESI) m/z: 431.2 (M+H+).

Provenance & Evidence