Diethyl Ether → HCID 59464110, compound

Participants

Reaction Conditions

Reaction Steps

5-[(3-Iodophenyl)amino]-N-(6-morpholin-4-ylpyridin-3-yl)-1,3,4-oxadiazole-2-carboxamide (Example 146) (610 mg, 1.24 mmol) was added portionwise to an ice-cooled suspension of sodium hydride (60% dispersion in oil) (119 mg, 2.97 mmol) in anhydrous DMF (5 mL) in dry glassware. The mixture was stirred at 0° C. for 10 minutes and ambient temperature for 30 minutes then recooled in an ice bath and [2-(chloromethoxy)ethyl](trimethyl)silane (0.482 mL, 2.73 mmol) was added dropwise. The mixture was allowed to warm up and stirred for 16 h. ether (60 mL) was added, and the mixture was washed with water (3×20 mL) and the aqueous extracts were re-extracted with ether (20 mL). The organic extracts were combined, dried and concentrated by evaporation and the residue was purified by chromatography, eluting with 0-20% ether/DCM to give the title compound (610 mg, 65%) as gum; 1H NMR δ 8.09 (1H, s), 7.94 (1H, s), 7.74 (1H, d), 7.59-7.40 (2H, m), 7.28 (1H, t), 6.86 (1H, d), 5.24-5.11 (1H, m), 3.80-3.48 (12H, m), 0.98-0.84 (4H, m), 0.10-0.05 (18H, m).

Provenance & Evidence