Hydrochloric Acid → HCID 69277010, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,2,2-trifluoro-N-(2-{4-methoxy-3-[(4-methylpiperazin-1-yl)sulfonyl]-phenyl}ethyl) acetamide (from Step 2), (1.25 g, 3.05 mmol) in MeOH (30 mL) and H2O (8 mL) was added K2CO3 (2.11 g, 15.3 mmol), and the solution was stirred at 60° C. for 2 h. After cooling to rt, the MeOH was evaporated under reduced pressure. The remaining aqueous mixture was extracted with CH2Cl2 (6×50 mL), and the combined organic phases were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was then dissolved in MeOH, and 4 equivalents of 1 N HCl in MeOH were added causing the formation of a white precipitate. The solvent was removed under reduced pressure, and the resulting solid was recrystallized from MeOH/Et2O to give the title compound [assumed to be the bis-HCl salt] as a white solid (457 mg, 48%). 1H NMR (400 MHz, CD3OD) δ 2.29 (s, 3H), 2.48 (broad t, 4H), 2.78 (dd, 2H), 2.87-2.92 (m, 2H), 3.23 (broad t, 4H), 3.91 (s, 3H) 7.16 (d, 1H), 7.47 (dd, 1H), 7.68 (d, 1H); ES-MS m/z (MH+) 314.2, HPLC RT (min) 0.70.

Provenance & Evidence