1-Pyrrolidineethanamine → HCID 86634764, compound

Participants

Reaction Steps

A vial was charged with 3-(5-bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-yloxy)-4-chlorobenzoic acid (0.050 g, 0.0942 mmol), 1-pyrrolidine ethanamine (0.013 g, 0.113 mmol), N,N-diisopropylethylamine (0.0328 mL, 0.188 mmol), and THF (3 mL). Diethyl cyanophosphononate (0.0239 g, 0.132 mmol) was added and the reaction was stirred for 4 hours at ambient temperature. The reaction mixture was concentrated and the residue was partitioned between water and ethyl acetate. The organic later was dried and concentrated, and the crude material was purified by preparative TLC using 5% ammoniated methanol in DCM. The isolated material was treated with 2M HCl in ether and the isolated solids were dried in vacuum to give the title compound (0.035 g, 51.5% yield) as a light yellow solid. 1H NMR (CDCl3) δ 8.99 (s, 1H), 8.36 (s, 1H), 7.96 (m, 2H), 7.57 (m, 1H), 7.25 (m, 1H), 7.15 (m, 3H), 6.70 (s, 1H), 6.30 (s, 1H), 3.85 (m, 4H), 3.35 (m, 2H), 2.93 (m, 6H), 2.14 (m, 4H).

Provenance & Evidence