Pyridine → HCID 68547866, compound

Participants

Reaction Steps

To a 50 mL round bottomed flask was added 2-chloro-4-((1R,2S)-2-hydroxy-1-(5-phenyl-1,3,4-oxadiazol-2-yl)propylamino)-3-methylbenzonitrile (300 mg, 0.82 mmol, pyridine (1 mL, 12.41 mmol) and methylene chloride (15 mL). Propionyl chloride (0.358 mL, 4.1 mmol) was then added dropwise and the mixture was stirred at room temperature for 48 h. The reaction mixture was then quenched with 10% aq HCl (15 mL) and methylene chloride (30 mL) was added. The phases were partitioned and the aqueous phase extracted with methylene chloride (30 mL) (×2). The combined organics were washed with a saturated solution of sodium hydrogen carbonate, dried (Na2SO4) and concentrated to furnish a yellow oil (0.382 g, 98%). 1H NMR (Acetone d6, 400 MHz) δ 8.01 (d, J=8 Hz, 2H), 7.64-7.53 (m, 4H), 7.02 (d, J=9 Hz, 1H), 5.73 (d, J=9 Hz, 1H), 5.69-5.62 (m, 1H), 5.44 (dd, J=5 and 8 Hz, 1H), 2.37 (s, 3H), 2.35 (q, J=7 Hz, 1H), 2.34 (q, J=7 Hz, 1H), 1.46 (d, J=6 Hz, 3H) and 1.03 (t, J=8 Hz, 3H).

Provenance & Evidence