Hydrochloric Acid → HCID 67520354, compound

Participants

Reaction Steps

To a solution of 3-benzothiazol-2-yl-5-[1-(1,4-dioxaspiro[4.5]dec-8-yl)-1H-pyrazol-4-yl]-pyridin-2-ylamine (0.750 g, 1.7 mmol) in dioxane (5 mL) was added 2 N HCl (1 mL), and the solution was stirred at RT for 1 h. The solvents were evaporated, and aq. satd. NaHCO3 solution (30 mL) was added to the residue. The mixture was extracted with CH2Cl2 (3×40 mL), and the combined extracts were washed with water, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by column chromatography on silica gel using EtOAc/Hexanes (1:1) to give the title compound as yellow solid. 1H NMR (400 MHz, CDCl3): δ=8.33 (d, J=2.2 Hz, 1H), 8.02 (dd, J=8.4, 0.4 Hz, 1H), 8.01 (d, J=2.4 Hz, 1H), 7.91 (ddd, J=8.4, 1.2, 0.4 Hz, 1H), 7.79 (d, J=0.6 Hz, 1H), 7.71 (d, J=0.6 Hz, 1H), 7.51 (ddd, J=8.4, 7.4, 1.2 Hz, 1H), 7.41 (ddd, J=8.0, 7.4, 1.4 Hz, 1H), 7.14 (brs, 2H), 4.72-4.64 (mc, 1H), 2.70-2.47 (m, 6H), 2.46-2.34 (m, 2H). MS(ES+): m/z=390.14 (100) [MH+]. HPLC: tR=3.13 min (polar—5 min, ZQ3).

Provenance & Evidence