1,2-Dichloroethane → HCID 11576363, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-[(2-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]-1-benzofuran-2-carboxylic acid (example 51) (0.100 g, 0.227 mmol), dimethylamine in THF (2M, 0.321 ml), EDC (0.132 g, 0.681 mmol), HOBt (0.065 g, 0.249 mmol) and TEA (0.090 ml, 0.681 mmol) in DMF (2 ml) was heated at 70° C. for 18 h. EtOAc was added and the mixture was washed with brine, evaporated and the residue was purified by flash chromatography (Horizons Biotage) using 50-65% EtOAc in hexane as eluent to give the title compound (0.054 g, 51%); 1H NMR (500 MHz CDCl3); δ 7.18 (dd, 1H), 7.14-7.10 (m, 3H), 7.08-7.02 (m, 2H), 6.99 (s, 1H), 6.91 (d, 1H), 6.84 (dd, 1H), 3.81 (t, 2H), 3.30 (bs, 3H), 3.14 (bs, 3H), 1.94-1.86 (m, 2H), 1.56-1.46 (m, 2H), 1.02 (t, 3H); 13C NMR (125 MHz CDCl3): δ 161.0, 159.5, 152.1, 151.0, 132.1, 131.4, 129.5, 129.5, 128.3, 127.1, 124.9, 121.6, 115.9, 111.9, 111.4, 111.2, 40.5, 30.5, 20.3, 13.8.; Mass Spectrum M+H+ 468.

Provenance & Evidence