Pyrrolidine → Benzo[b]thiophene-2-sulfonic acid {2-[2-methoxy-5-(2-pyrrolidin-1-yl-ethanesulfonyl)-benzenesulfonylamino]-phenyl}-amide

Participants

Reaction Steps

To a solution of benzo[b]thiophene-2-sulfonic acid [2-(5-ethenesulfonyl-2-methoxybenzenesulfonylamino)phenyl]-amide (0.2 mmol, prepared as in Example 19) in dry THF (2 mL) was added 0.2 mL of pyrrolidine. The resulting reaction mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with DCM (10 mL) and was washed with saturated sodium chloride aqueous solution (25 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with EtOAc then DCM/methanol/AcOH (100:2:1 to 100:10:2) to furnish 121 mg of benzo[b]thiophene-2-sulfonic acid {2-[2-methoxy-5-(2-pyrrolidin-1-yl-ethanesulfonyl)-benzenesulfonylamino]phenyl} amide. LC: Tr 0.94 min; MS: 636.8 (M+1)+. 1H NMR (CDCl3, 400 MHz): δ 1.68 (m, 4H), 2.38 (m, 4H), 2.78(t, 2H), 3.28 (t, 2H), 4.20 (s, 3H), 6.76 (d, 1H), 6.96 (d, 1H), 7.14 (t, 1H), 7.21 (d, 1H), 7.36 (d, 1H), 7.41 (t, 1H), 7.49(t, 1H), 7.60 (s, 1H), 7.79 (d, 1H), 7.83 (d, 1H), 8.07 (d, 1H), 8.26 (d, 1H) ppm.

Provenance & Evidence