Sodium;3-oxidodioxaborirane;tetrahydrate → HCID 66612604, compound

Participants

Reaction Conditions

Reaction Steps

Sodium perborate tetrahydrate (130 mg, 0.84 mmol, 2.4 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 yellow suspension was heated to 60° C. for 15 h. The cooled reaction mixture was diluted with a saturated solution of sodium bicarbonate (50 mL) and extracted with dichloromethane (3×30 mL). The combined organic layers were dried (sodium sulfate), 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 (90 mg, 82% yield): mp 199-201° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.15 (d, J=2 Hz, 1H), 8.73 (dd, J=6, 2 Hz, 1H), 8.32 (dt, J=8, 2 Hz, 1H), 7.46 (dd, J=8, 5 Hz, 1H), 3.94 (s, 3H), 3.59 (t, J=7 Hz, 2H), 3.33 (t, J=7 Hz, 2H), 3.09 (s, 3H); ESIMS m/z 327 ([M+H]+). Compounds 33, 36, 37, 40, 43, 46, 52, 76 were prepared as described in Example 11.

Provenance & Evidence