Hydroxylamine → 6-[2-(4-Phenyl-piperazin-1-yl)-acetylamino]-benzo[b]thiophene-2-carboxylic acid hydroxyamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-(2-chloro-acetylamino)-benzo[b]thiophene-2-carboxylic acid methyl ester (75 mg, 0.26 mmol) in DMF (2 mL) was added amine (85.8 mg, 0.52 mmol). The reaction mixture was heated to 50° C. After 24 h, NH2OH (50% aq., 1 mL) was added to the solution. The solution was stirred until the disappearance of starting material. After removal of solvent, MeOH/H2O was added until a precipitate forms. The solid was filtered yielding the desired amide. 1H NMR (DMSO-d6) δ 11.32 (br s, 1H), 9.97 (s, 1H), 9.28 (br s, 1H), 8.39 (s, 1H), 7.85-7.72 (m, 2H), 7.55 (d, J=7.0 Hz, 1H), 7.24-7.10 (m, 2H), 6.94-6.84 (m, 2H), 6.72 (t, J=7.0 Hz, 1H), 3.24-3.05 (m, 5H), 2.70-2.58 (m, 4H). MS (EI): cal'd (MH+) 411.14, exp (MH+) 411.33.

Provenance & Evidence