Hydrogen Peroxide → HCID 56953577, compound

Participants

Reaction Steps

A stirred suspension of [5-[2-(4-ethoxycarbonyl-4-methyl-1-piperidyl)pyrimidin-5-yl]-2-(ethylcarbamoylamino)-1,3-benzothiazol-7-yl]boronic acid (166 mg, 0.286 mmol) in aqueous NaOH solution (2 M, 1.3 mL) was treated with excess hydrogen peroxide (27.5% aqueous solution, 0.45 mL) and kept at rt for 3 days by which time LCMS showed complete reaction. The resultant mixture was diluted with water (30 mL) and acidified by the addition of a small amount of conc. sulfuric acid. The precipitated solid was collected by filtration, washed with water (10 mL) and dried in vacuo to give Compound 26 as a white solid (102 mg, 78% yield). 1H NMR (DMSO-d6): δ 10.37 (1H, s), 8.67 (2H, s), 7.37 (1H, s), 6.85 (1H, s), 6.77 (1H, t, J=5.86 Hz), 4.30 (2H, dt, J=13.75, 4.56 Hz), 3.36 (2H, ddd, J=13.34, 9.92, 3.07 Hz), 3.22 (2H, p, J=6.69 Hz), 2.04 (2H, dt, J=13.63, 3.69 Hz), 1.42 (2H, ddd, J=13.55, 10.29, 3.91 Hz), 1.22 (3H, s), 1.13 (3H, t, J=7.19 Hz). m/z: 457 [M+H]+.

Provenance & Evidence