Dimethyl Sulfoxide → HCID 58923365, compound

Participants

Reaction Steps

A suspension of KH (about 3 mg, 30-35% by weight in mineral oil) was added to a solution of N,N-dimethylethanolamine (14 mg, 0.16 mmol) and 6-fluoro-1-hydroxy-3-morpholin-4-yl-10H-acridin-9-one (25 mg, 0.08 mmol) in DMSO (1.0 mL), and the reaction mixture was heated at reflux for 4 hours. After cooling, the mixture was diluted with EtOAc and sat. NH4Cl. The organic layer was washed six times with water. The organics were dried (Na2SO4), then concentrated. The concentrate was purified via flash chromatography to yield 4 mg (13%). 1H NMR (CDCl3, 400 MHz) δ: 12.94 (s, 1H), 8.11 (d, 1H), 6.93 (d, 1H), 6.81 (s, 1H), 6.25 (d, 1H), 4.17 (t, 3H), 3.86-3.84 (m, 4H), 3.37-3.35 (m, 4H), 2.80 (t, 2H), 2.39 (s, 6H). LRMS (APCI, positive): Da/e 384.5 (m+1).

Provenance & Evidence