Dichloromethane → HCID 86687544, compound

Participants

Reaction Steps

A round-bottom flask was charged with 3-amino-4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (Intermediate NNNN; 42.59 mg, 0.071 mmol), DCM (1 mL) and TFA (0.5 mL). The mixture was stirred for 1 h, then diluted with MeOH and concentrated. The residue was taken up in DCM and loaded onto a 500-mg SCX-2 ion exchange column (Biotage, LLC). The column was eluted with MeOH, then with 2N ammonia in methanol. The basic fractions were combined and concentrated. The residue was concentrated from DCM to give 3-amino-4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)quinoline-7-sulfonamide (30 mg, 0.062 mmol, 88% yield) as a light-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm=12.72 (br. s., 1H), 8.65 (s, 1H), 8.22 (d, J=2.0 Hz, 1H), 7.59 (dd, J=2.0, 8.9 Hz, 1H), 7.52-7.44 (m, 2H), 7.42-7.35 (m, 1H), 7.24 (d, J=4.7 Hz, 1H), 7.08 (d, J=8.9 Hz, 1H), 6.81 (d, J=4.6 Hz, 1H), 5.62 (s, 2H), 3.75 (s, 3H); m/z (ESI) 481.2 (M+H)+.

Provenance & Evidence