Water → HCID 58817501, compound

Participants

Reaction Steps

The sulfonamide 11-3 (67 mg, 0.11 mmol) was dissolved in 3.0 mL of dichloromethane, 100 μL of water, and 150 μL of dimethyl sulfide at ambient temperature. Trifluoroacetic acid (2.0 mL) was then added via pipette to afford a dark yellow solution. The reaction was stirred for 5 hours until completion via LCMS analysis. The reaction solution was concentrated and the residue partitioned between ethyl acetate (15 mL) and half-saturated NaHCO3 solution (100 mL). The layers were separated and the aqueous layer was extracted several times with ethyl acetate (10×30 mL). The combined organic layers were washed with brine, separated, dried (Na2SO4) and concentrated in vacuo to afford a yellow solid. Reverse-phase chromatography (0.01% TFA present) (90% water to 90% acetonitrile) followed by free-base extraction into ethyl acetate and concentration afforded 11-4 as a yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 12.17 (s, 1 H), 11.62 (s, 1 H), 8.55 (s, 1 H), 7.74 (d, 1 H, J=7.2 Hz), 7.53 (m, 3 H), 7.38 (d, 1 H, J=8.1 Hz), 7.32 (d, 1H, J=1.5 Hz), 7.25 (app t, 1 H, J=7.5 Hz), 7.11 (dd, 1 H, J=8.7, 1.2 Hz), 4.48 (s, 2H), 3.41 (m, 2 H), 3.05 (m, 2 H), 2.50 (m, 4 H).

Provenance & Evidence