1,2-Dichloroethane → HCID 86267640, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of Example B (0.054 g, 0.427 mmol) in DCE (4 mL) was treated with oxalyl chloride (0.037 mL, 0.427 mmol), heated at 83° C. for 2 h, cooled to RT and added drop-wise to a solution of Example A6 (0.1 g, 0.355 mmol) in THF (4 mL) and pyridine (0.144 mL, 1.777 mmol). The mixture was stirred at RT for 2 h, treated with satd. NaHCO3, extracted with EtOAc (3×) and the combined organics were dried over MgSO4, concentrated to dryness, triturated with MeCN, and the solid collected via filtration and dried to afford 3,3-dimethyl-N-((6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)cyclobutanecarboxamide (134 mg, 87%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.06 (s, 1H), 10.69 (s, 1H), 8.35 (d, J=5.7 Hz, 1H), 8.25 (s, 1H), 7.95 (s, 1H), 7.90 (d, J=8.8 Hz, 1H), 7.61 (d, J=8.8 Hz, 1H), 7.16 (d, J=2.4 Hz, 1H), 6.60 (dd, J=5.7, 2.4 Hz, 1H), 3.84 (s, 3H), 3.24 (m, 1H), 2.26 (s, 3H), 2.02-1.87 (m, 4H), 1.13 (s, 3H), 1.05 (s, 3H); MS (ESI) m/z: 435.2 (M+H+).

Provenance & Evidence