Diethyl Ether → HCID 20607424, compound

Participants

Reaction Steps

Then 5-[(S)-2-amino-1-propyloxy]-2-chloro-3-(4-vinylpyridinyl)pyridine p-toluenesulfonic acid 13 was prepared as follows. A solution of the product 13B (70 mg, 0.242 mmol) in ethyl acetate (1 mL) was treated with p-toluenesulfonic acid monohydrate (51 mg, 0.266 mmol) and stirred for 5 minutes. Next, ethyl ether (30 mL) was added and stirred for an additional 5 minutes. The ether was decanted and the procedure was repeated. It was then dried under vacuum to provide 13 as a light yellow solid. mp 69-71° C.; MS (CI/NH3) m/e 290 (M+H)+; 1H NMR (D2O, 500 MHz) δ: 1.48 (d, J=7 Hz, 3H), 2.35 (s, 3H), 3.87 (m, 1H), 4.14 (m, 1H), 4.31 (dd, J=4, 10 Hz, 1H), 7.10 (d, J=6 Hz, 2H), 7.29 (d, J=8 Hz, 2H), 7.45 (d, J=16 Hz, 2H), 7.64 (d, J=8 Hz, 2H), 7.68 (d, J=3 Hz, 1H), 7.93 (d, J=3 Hz, 1H), 8.45 (d, J=6 Hz, 2H); Analysis calculated for C15H16N3ClO.1.65C7H8O3S.1.15H2O: C, 53.63; H, 5.34; N, 7.07; Found: C, 53.83; H, 5.25; N, 6.77; [α]25D=+1.3° (c=0.75, MeOH).

Provenance & Evidence