Methylamine → HCID 90332526, compound

Participants

Reaction Steps

A solution of 5-bromo-2-(cyclopent-1-en-1-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxylic acid (3.5 g, 7.70 mmol), HOBT (1.6 g, 11.55 mmol) and EDCI (2.2 g, 11.55 mmol) in dry DMF (40 mL) was stirred at 25° C. After 2 hours, Et3N (2.4 g, 23.11 mmol) and MeNH2 (1.6 g, 23.11 mmol) were added to the mixture and then stirred overnight. The solvent was removed by vacuum, the mixture was washed with H2O (50 mL) and extracted with EtOAc (50 mL*3), and dried over Na2SO4. After concentration, the residue was purified by column chromatography (DCM) to give the product of 5-bromo-2-(cyclopent-1-en-1-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (2 g, yield: 56%). 1H-NMR (CDCl3, 400 MHz) δ 8.00 (s, 1H), 7.59 (s, 1H), 6.70 (t, J=3.2 Hz, 1H), 5.95 (s, 1H), 3.31 (s, 3H), 3.30 (s, 3H), 3.06 (s, 3H), 2.76˜2.81 (m, 2H), 2.58˜2.62 (m, 2H), 2.07 (t, J=7.6 Hz, 2H). MS (M+H)+: 427/429.

Provenance & Evidence