4-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid → N-[4-[5-(Cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(pent-1-yn-1-yl)-benzenesulfonamide

Participants

Reaction Steps

1.07 g of 2-(pent-1-yn-1-yl)-benzenesulfonamide and 0.94 g of 3-[N-dimethylaminopropyl]-N-ethylcarbodiimide hydrochloride as well as 0.6 g of 4-dimethylaminopyridine are added to a solution of 2.0 g of 4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxy-benzoic acid in 50 ml of methylene chloride. The reaction mixture is stirred for 20 hours under argon and then diluted with 50 ml of methylene chloride. The methylene chloride phase is washed in a separating funnel twice with 1N hydrochloric acid and once with water. The methylene chloride phase is dried over magnesium sulfate and concentrated by evaporation at 20 torr and 40°. The residue is chromatographed on 80 g of silica gel (Merck Si60, 40-63 μm), ethyl acetate being used as eluant. The fractions containing the product are concentrated by evaporation at 20 torr and 40° to yield 2.2 g of the title compound in the form of a white amorphous solid. 1H-NMR (400 MHz, DMSO-d6): 8.76 (s, b, 1H); 8.00 (d, 1H); 7.56 (m, 2H); 7.44 (m, 4H); 7.21 (d, 1H); 7.16 (d, d, 1H); 7.08 (d, 1H); 6.91 (s, 1H); 5.07 (m, 1H); 3.94 (s, 2H); 3.88 (s, 3H); 3.66 (s, 3H); 2.33 (t, 2H); 1.90-1.53 (m, 8H); 1.47 (m, 2H); 0.89 (t, 3H).

Provenance & Evidence