Trifluoroacetic acid → 2-(1-(5-Propylpyrimidin-2-yl)piperidin-4-yloxy)-6-(1,2,3,6-tetrahydropyridin-4-yl)benzo[d]thiazole

Participants

Reaction Steps

To a solution of tert-butyl 4-(2-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazol-6-yl)-5,6-dihydropyridine-1(2H)-carboxylate (166 mg, 0.310 mmol) in CH2Cl2 (3 mL) was added TFA (0.358 mL, 4.65 mmol). Upon completion of addition, the reaction mixture was stirred at rt for 3 hrs. After this time, the reaction mixture was diluted with CH2Cl2 (10 mL) and washed with aq NaOH (1 N, 5 mL) and brine (5 mL) and then dried (Na2SO4). The resulting mixture was filtered and concentrated under reduced pressure to afford Compound 1E as a light yellow solid (124 mg, 0.285 mmol, 92% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 8.17 (2H, s), 7.59-7.68 (2H, m), 7.42 (1H, dd, J=8.5, 1.9 Hz), 6.11-6.21 (1H, m), 5.39-5.55 (1H, m), 4.23 (2H, ddd, J=13.3, 6.8, 3.9 Hz), 3.62-3.77 (2H, m), 3.56 (2H, q, J=2.6 Hz), 3.14 (2H, t, J=5.7 Hz), 2.46-2.55 (2H, m), 2.41 (2H, t, J=7.6 Hz), 2.13-2.24 (2H, m), 1.88-2.00 (2H, m), 1.52-1.61 (3H, m), 0.95 (3H, t, J=7.5 Hz).

Provenance & Evidence