Triethylamine → HCID 18506825, compound

Participants

Reaction Steps

2-Amino-3-methylpyridine (19-1, 0.281 g, 2.60 mmol) was stirred in 6 mL anhydrous DCM under N2. Thiophosgene (0.198 mL, 2.60 mmol) was added followed by the addition of triethylamine (1.09 mL, 7.79 mmol) and an additional 4 mL anhydrous DCM. After 30 min 2,2-dimethoxy-2-pyridin-4-yl-ethylamine (0.430 g, 2.36 mmol, Ganellin, C. R.; Hosseini, S. K.; Khalaf, Y. S.; Tertiuk, W.; Arrang, J.-M.; et al. J.Med.Chem. 1995, 38, 3342-3350) was added as a solution in 2 mL anhydrous DCM. After 16 h the reaction was quenched with sat NaHCO3 (aq) and extracted 3× with DCM. The combined organic extracts were dried over Na2SO4, filtered, and concentrated to provide the pure titled compound as a tan solid. 1H NMR (CDCl3) δ11.88 (s, 1H), 8.65 (d, 2H, J=6.0 Hz), 7.76 (m, 2H), 7.50 (d, 2H, J=6.2 Hz), 7.44 (m, 1H), 6.87 (dd, 1H, J=5.1, 7.3 Hz), 4.22 (d, 2H, J=5.0 Hz), 3.29 (s, 6H), 2.22 (s, 3H).

Provenance & Evidence