Fumaric Acid → HCID 66629517, compound

Participants

Reaction Steps

The compound of step 4a was dissolved in anhydrous MeOH and brought to 0° C. with stirring. Fumaric acid was dissolved in MeOH with sonication and added dropwise to the solution containing amine. The mixture was warmed to room temperature with stirring. After 30 minutes the solvent was evaporated in vacuo and the remaining solid was vacuum filtered. The solid was then recrystallized with MeOH/Et2O to give the desired product as a white powder (21% yield). m.p.=124-125° C. [α]25D =-3.9° (c=1, MeOH). MS (DCI/NH3) m/e 193 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 8.43 (br s, 1H, 8.33 (d, J=4.5 Hz, 1H), 7.88-7.84 (m, 1H), 7.3 (dd, J=8.82, 5.15 Hz, 1H), 6.58 (s, 2H), 4.59 (dd, J=11, 3 Hz, 1H), 4.42 (dd, J=11, 5.98 Hz, 1H), 4.05-3.9 (m, 1H), 3.82-3.74 (m, 1H, 3.343.22 (m, 1H), 3.05 (s, 3H), 2.47-2.37 (m, 1H), 2.30-2.06 (m, 3H). Analysis calculated for C11H16N2O.C4H4O4 : C, 58.43; H, 6.54; N, 9.09; Found: C, 58.32; H, 6.67; N, 8.99.

Provenance & Evidence