2,6-Dimethylmorpholine, cis- → HCID 71280529, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromo-N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (42h) (25 mg, 0.051 mmol), cis-2,6-dimethylmorpholine (9 mg, 0.077 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (4 mg, 0.01 mmol), tris(dibenzylideneacetone)dipalladium(0) (2 mg, 0.003 mmol), and sodium t-butoxide (10 mg, 0.102 mmol) in anhydrous dioxane (1 mL) was heated in the microwave at 125° C. for 25 minutes. The reaction was cooled to room temperature and filtered through a plug of celite. The solvent was concentrated and the crude product was purified by reverse phase preparative HPLC to afford N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-((2S,6R)-2,6-dimethylmorpholino)imidazo[1,2-a]pyridine-3-carboxamide (F96). 1H NMR (400 MHz, d6-DMSO) δ 10.17 (s, 1H), 8.95 (d, J=1.6 Hz, 1H), 8.64 (s, 1H), 8.03 (d, J=1.6 Hz, 1H), 7.84 (dd, J=1.6, 8.0 Hz, 1H), 7.79-7.71 (m, 2H), 7.50 (d, J=8.0 Hz, 1H), 3.91-3.86 (m, 1H), 3.76-3.71 (m, 2H), 3.54-3.51 (m, 2H), 3.23-3.03 (m, 4H), 2.36 (s, 3H), 2.31-2.25 (m, 2H), 1.17 (s, 3H), 1.15 (s, 3H). MS m/z 522.22 (M+1)+.

Provenance & Evidence