Furfurylamine → HCID 58820552, compound

Participants

Reaction Steps

A solution of Example 49 (241 mg, 0.49 mmol) and carbonyldimidazole (0.54 mmol, 88.2 mg) in THF (anhydrous, 15 ml) was stirred for 1 hr at r.t. Then was added dropwise a solution of furfurylamine (96.1 mg, 0.99 mmol) in THF (2 ml) and the mixture stirred at r.t. for 12 hr. Then the reaction mixture concentrated and the yellow oil purified on SiO2 (ethyl acetate:hexanes 1:5) to afford the title compound as a white solid (194 mg, 343 mmol): 1H NMR (400 MHz, d6-DMSO) δ 9.03 (t, 1H), 7.82 (d, J=8.6 Hz, 2H), 7.53 (d, J=8.2 Hz, 2H), 7.26 (d, J=8.2 Hz, 2H), 7.20–7.17 (m, 2H), 7.09–7.04 (m, 2H), 6.36 (d, J=4.0 Hz, 1H), 6.25 (d, J=4.0 Hz, 1H), 4.69–4.65 (m, 1H), 4.46–4.44 (m, 2H), 3.91 (q, 2H), 3.39–3.36 (m, 1H), 3.19–3.13 (m, 1H), 2.90–2.79 (m, 4H), 2.28–2.18 (m, 3H), 1.13–1.08 (m, 1H), 1.08 (t, 3H) ppm. ESI-MS m/z 567 (M+H)+. HPLC (99%). Anal. calcd. for C34H31N2O5F 0.41H2O: C, 71.14; H, 5.59; N, 4.88. Found: C, 71.14; H, 5.66; N, 4.84.

Provenance & Evidence