Trifluoroacetic acid → 7-Chloro-4-(1-piperazinyl)-2-quinolinamine

Participants

Reaction Steps

To a stirred sloution of 4-[7-chloro-2-[[(1,1-dimethylethoxy)carbonyl]amino]-4-quinolinyl]-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (2 g, 4.33 mmol) in CH2Cl2 (30 mL) was added TFA (4 mL) at rt. The reaction mixture was kept at reflux for 4 h, then cooled to rt. After removal of the solvent and excess TFA, the mixture was diluted with CH2Cl2, and treated with NaOH (10%) to pH 12. The mixture was extracted with CH2Cl2, washed with brine, and dried over Na2SO4. Concentration in vacuo afforded the product as a free base (1.13 g, 98%). LC-MS: 262 (M++1). 1H NMR (DMSO-d6): 62.90 (s, 8H), 6.20 (s, 1H), 6.4 (s, 2H) 7.08 (d, 1H), 7.35 (s, 1H), 7.68 (d, 1H).

Provenance & Evidence