Trifluoroacetic acid → HCID 11720248, compound

Participants

Reaction Steps

2,4-Dichloro-N-{1-methyl-1-[1-((tert-butoxycarbony)ethylaminosulfonyl)-4-pyridin-2-ylpiperidin-4-yl]ethyl}benzamide (VI-2, 35 mg, 0.061 mmol) was dissolved in DCM (1.6 mL) and cooled in an ice bath. TFA (0.4 mL) was added dropwise and upon completion of the addition the reaction mixture was stirred in a nice bath for 0.5 h then allowed to warm to roomtemperature and stirred at room temperature for 12 h. The volatile components of the reaction mixture were removed in vacuo then saturated aqueous sodium hydrogen carbonate solution added dropwise. The mixture was extracted three times with EtOAc. The combined organic phase was dried (Na2SO4) and the solvent removed in vacuo to give 2,4-dichloro-N-{1-methyl-1-[1-(ethylaminosulfonyl)-4-pyridin-2-ylpiperidin-4-yl]ethyl}benzamide (VI-3). 1H NMR (CD3OD, 500 MHz), δ 8.62 (d, J=4.1 Hz, 1H), 7.93 (m, 1H), 7.65 (d, J=8.0 Hz, 1H), 7.48 (d, J=1.8 Hz, 1H), 7.37 (m, 1H), 7.30 (d, J=8.0 Hz, 1H), 3.66 (s, 2H), 3.48 (m, 2H), 3.00 (q, J=7.0 Hz, 2H), 2.94 (m, 2H), 2.50 (m, 2H), 2.04 (m, 2H), 1.12 (t, J=7.0 Hz, 3H); MS 472 (M+H).

Provenance & Evidence