4-{5-[(4-Chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester → 4-Chloro-benzo[b]thiophene-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide

Participants

Reaction Steps

A mixture of 4-{5-[(4-chloro-benzo[b]thiophene-2-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester (75 mg, 0.16 mmol) in 15 mL of dichloromethane and 5 mL of TFA was stirred at room temperature for 2 hr. The reaction mixture was taken up in 100 mL of EtOAc and washed with 100 mL of 1N NaOH, brine and dried over anhydrous sodium sulfate. The solvent was removed and the residue was triturated with diethyl ether and hexanes (1:1 ratio), followed by filtration, to afford the product 4-chloro-benzo[b]thiophene-2-carboxylic acid (6-piperazin-1-yl-pyridin-3-yl)-amide, (50 mg, 85% yield) as an off white solid. LCMS for C18H17ClN4OS calcd. (m/e) 372, observed 373 (M+H).

Provenance & Evidence