Acetic Acid → HCID 58109530, compound

Participants

Reaction Steps

A mixture of 6-(2-fluorophenyl)-3-(6-(4-fluorophenyl)pyridin-2-yl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (30 mg, 0.07 mmol), NaOAc (9 mg, 0.11 mmol) in HOAc (4 mg, 0.07 mmol), CH3CN (2 mL), H2O (0.1 mL) and CH2Cl2 (2 mL) was stirred at rt for 5 min. A solution of 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione (37 mg, 0.11 mmol) in CH3CN (0.5 mL) was added slowly. The mixture was stirred for 20 min and heated to 40° C. for 2 h. The reaction was quenched with aq NaHSO3 and extracted with CH2Cl2. The organic layer was dried with Na2SO4, concentrated to afford the crude product. Purification afforded 3-(5-chloro-6-(4-fluorophenyl)pyridin-2-yl)-6-(2-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (15 mg, 48%). LC-MS Method 3, tR=1.331 min, m/z=445. 1H NMR (CDCl3, 400 Hz): 2.40 (m, 3H), 2.84 (m, 1H), 3.40 (m, 1H), 3.66 (m, 1H), 3.82 (m, 1H), 4.26 (m, 1H), 7.10 (m, 3H), 7.18 (m, 1H), 7.34 (m, 1H), 7.50 (m, 1H), 7.68 (m, 2H), 7.76 (m, 1H), 8.01 (m, 1H).

Provenance & Evidence