Trifluoroacetic acid → HCID 57991866, compound

Participants

Reaction Steps

TFA (1 mL) was added to a solution of tert-butyl (R)-4-(5-(3-fluoroisoquinolin-6-yl)-1,3,4-thiadiazol-2-yl)-1-(6-(trifluoromethyl)pyridin-3-yl)butan-2-ylcarbamate (85 mg, 155 μmol) in DCM (1 mL), and the mixture was stirred at room temperature for 2 hours. The mixture was concentrated under reduced pressure, and the resulting yellow oil was purified by reversed phase HPLC (Shimadsu Valiant, Phenomenex Gemini C18 5 μm 100×30 mm, 5% to 50% H2O/MeCN, 0.1% TFA) to deliver a colorless oil. The oil was dissolved in MeOH, absorbed onto ISOLUTE Si-TsOH(SCX-3) (5 g), and washed with MeOH (50 mL) and then with 2 N NH3 in MeOH (30 mL) providing (2R)-4-(5-(3-fluoroisoquinolin-6-yl)-1,3,4-thiadiazol-2-yl)-1-(6-(trifluoromethyl)pyridin-3-yl)butan-2-amine (57 mg, 82%) as a light yellow solid. 1H NMR (300 MHz, CD3OD) δ ppm 1.88-2.16 (m, 2 H), 2.85 (d, J=13.6, 7.6 Hz, 1 H), 3.02 (dd, J=13.6, 5.8 Hz, 1 H), 3.15-3.28 (m, 1 H), 3.34-3.49 (m, 2 H), 7.53 (s, 1 H), 7.76 (d, J=8.0 Hz, 1 H), 7.95 (d, J=8.0 Hz, 1 H), 8.15 (dd, J=8.7, 1.3 Hz, 1 H), 8.23 (d, J=8.7 Hz, 1 H), 8.45 (s, 1 H), 8.63 (s, 1 H), 9.05 (s, 1 H). LCMS (API-ES) m/z: 470.0 (M+Na+).

Provenance & Evidence