2,1,3-Benzothiadiazole, 4-chlorosulfonyl- → HCID 11606481, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-4-amino-6-bromo-2-(2-phenyl-propyl)-isoindole-1,3-dione (30 mg, 0.08 mmol) and benzo[1,2,5]thiadiazole-4-sulfonyl chloride (150 mg, 0.64 mmol) was heated to 170° C. forming a melt and stirred for 2 h. The mixture was allowed to cool, and the solidified residue was dissolved in EtOAc, and the solution was washed with satd. aq. NaHCO3, dried (Na2SO4), and concentrated. Purification by flash chromatography (EtOAc/hexanes) gave the desired sulfonamide as a tan solid (30 mg, 64%). HPLC: RT=11.01 min. MS (ESI−): mass calcd. for C23H17BrN4O4S2, 555.99; m/z found, 555/557 [M−H]−. 1H NMR (400 MHz, CDCl3): 9.59 (br s, 1H), 8.39 (dd, J=7.0, 1.0, 1H), 8.27 (dd, J=8.8, 1.0, 1H), 8.08 (d, J=1.4, 1H), 7.75 (dd, J=8.8, 7.1, 1H), 7.47 (d, J=1.3, 1H), 7.27-7.22 (m, 2H), 7.21-7.17 (m, 3H), 3.78 (dd, J=13.6, 8.1, 1H), 3.68 (dd, J=13.6, 7.81, 1H), 3.26 (sextet, J=7.4, 1H), 1.26 (d, J=7.0, 3H).

Provenance & Evidence