Pyridine → HCID 90403467, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-(bicyclo[2.2.1]heptan-2-yl)acetamide (0.069 g, 0.449 mmol) in DCE (3 mL) was treated with oxalyl chloride (0.039 mL, 0.449 mmol) and heated at 80° C. for 3 h. The mixture was cooled to RT, added drop wise to a solution of Example A2 (0.10 g, 0.374 mmol) and pyridine (0.151 mL, 1.871 mmol) in THF (3 mL) and stirred at RT for 3 days. The mixture was concentrated to dryness and purified via silica gel chromatography (EtOAc, MeOH/DCM). The material was treated with MeCN, the solid collected via filtration and dried to afford 2-(bicyclo[2.2.1]heptan-2-yl)-N-((5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)acetamide (138 mg, 81%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.10 (s, 1H), 10.82 (s, 1H), 8.37 (d, J=5.7 Hz, 1H), 8.26-8.25 (m, 2H), 8.08 (d, J=9.0 Hz, 1H), 7.95 (d, J=0.7 Hz, 1H), 7.72 (dd, J=9.0, 2.9 Hz, 1H), 7.22 (d, J=2.4 Hz, 1H), 6.70 (dd, J=5.7, 2.4 Hz, 1H), 3.83 (s, 3H), 2.36 (dd, J=14.7, 7.8 Hz, 1H), 2.23 (dd, J=14.7, 7.8 Hz, 1H), 2.21 (m, 1H), 1.94 (m, 1H), 1.85 (m, 1H), 1.45-1.38 (m, 3H), 1.31 (m, 1H), 1.11-1.07 (m, 4H); MS (ESI) m/z: 447.3 (M+H+).

Provenance & Evidence