Sodium;3-oxidodioxaborirane;tetrahydrate → HCID 66613909, compound

Participants

Reaction Conditions

Reaction Steps

Sodium perborate tetrahydrate (52 mg, 0.34 mmol, 1.0 equiv) was added to a stirred solution of N-methyl-3-(methylthio)-N-(5-(pyridin-3-yl)-1,3,4-thiadiazol-2-yl)propanamide (100 mg, 0.34 mmol, 1.0 equiv) in glacial acetic acid (1.8 mL) at 23° C. The resulting suspension was stirred at 23° C. for 3 h. The reaction mixture was diluted with a saturated solution of sodium bicarbonate (50 mL) and extracted with dichloromethane (5×20 mL). The combined organic layers were dried (Na2SO4), gravity-filtered, and concentrated by rotary evaporation. The residue was rinsed with cold ethyl acetate and vacuum-filtered to afford the title compound as an off-white powder (82 mg, 78% yield): mp 138-140° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.12 (d, J=2 Hz, 1H), 8.71 (dd, J=5, 2 Hz, 1H), 8.34 (m, 1H), 7.56 (dd, J=8, 5 Hz, 1H), 3.80 (s, 3H), 2.90-3.30 (m, 3H), 2.62 (s, 3H); ESIMS m/z 311 ([M+H]+). Compounds 32, 45, 51, and 77 were prepared as described in Example 10.

Provenance & Evidence