Butyryl chloride → HCID 44199939, compound

Participants

Reaction Steps

To a solution of 2-chloro-4-((1R,2S)-1-(5-(3-chloro-4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)-2-hydroxypropylamino)-3-methylbenzonitrile (example 37) (96.5 mg, 0.23 mmol) in pyridine (0.6 mL) and CH2Cl2 (4 mL) was added n-butyryl chloride (0.12 mL, 1.15 mmol). Upon complete addition the reaction mixture was stirred for 23 h, then quenched with 10% aqueous HCl (10 mL). The mixture was partitioned between H2O (25 mL) and CH2Cl2 (30 mL). The aqueous layer was extracted with CH2Cl2 (20 mL). The combined organic extracts were washed with NaHCO3 (30 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to provide an orange/brown viscous oil, which was purified by flash chromatography over silica gel (20-25% EtOAc in hexanes) to provide the title compound as an off white solid (116 mg, 90%); 1H NMR (400 MHz, d6-acetone, δ in ppm) 8.11 (d, J=2.0 Hz, 1 H), 8.03 (dd, J=2.2, 8.4 Hz, 1 H), 7.54 (d, J=8.6 Hz, 1 H), 7.49 (d, J=8.4 Hz, 1 H), 7.01 (d, J=8.8 Hz, 1 H), 5.74 (d, J=9.0 Hz, 1 H), 5.67 (dq, J=5.7, 6.5 Hz, 1 H), 5.45 (dd, J=5.7, 8.6 Hz, 1 H), 2.67 (t, J=7.4 Hz, 2 H), 2.33-2.28 (m, 2 H), 1.83-1.72 (m, 2 H), 1.66-1.52 (m, 2 H), 1.47 (d, J=6.5 Hz, 3 H), 1.04 (t, J=7.4 Hz, 3 H), 0.86 (t, J=7.4 Hz, 3 H).

Provenance & Evidence