Diisopropylethylamine → HCID 86688146, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of quinoline-5-carboxylic acid (0.054 g, 0.312 mmol), DIPEA (0.054 mL, 0.312 mmol), and DPPA (0.067 mL, 0.312 mmol) in 1,4-dioxane (2 mL) was stirred at rt for 1 h. (S)-(4-(Trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methanamine hydrochloride (Intermediate 1) (0.100 g, 0.312 mmol) was added, and the resulting mixture was heated at 85° C. for 24 h. The reaction mixture was cooled, concentrated, and purified by ISCO (Silica gel, 0-75% EtOAc/hexanes) to give the title compound. 1H-NMR (300 MHz, MeOH-d4): δ ppm 8.93 (d, J=4.5 Hz, 1H), 8.82 (d, J=3.5 Hz, 1H), 8.46 (d, J=8.5 Hz, 1H), 8.18 (d, J=8.0 Hz, 1H), 7.85 (d, J=7.3 Hz, 1H), 7.75-7.83 (m, 1H), 7.71 (d, J=7.7 Hz, 1H), 7.54-7.68 (m, 5H), 7.51 (dd, J=8.6, 4.2 Hz, 1H), 6.67 (s, 1H). MS (ESI pos. ion) m/z: 491.0 (M+H).

Provenance & Evidence