Morpholine → HCID 21884596, compound

Participants

Reaction Steps

A solution of 2-[3-(6-chlorocarbonylbenzoxazol-2-yl)phenyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid benzyl ester (50 mg, 0.09 mmol) in THF (1 ml) was added to a solution of tetrahydrofurfurylamine (14 mg, 0.14 mmol) in THF (1 ml) containing polymer bound morpholine (2.5 mmol g−1, 72 mg). After shaking overnight, polymer bound isocyanate (2.0 mmol g−1, 90 mg) was added and the reaction shaken for 4 h. The reaction was filtered and the solvent removed under reduced pressure. The residue was suspended in dioxane and palladium on carbon was added (spatula tip). The reaction vessel was purged with hydrogen and stirred at room temperature overnight. The reaction was filtered through celite and the filtrate concentrated to give the title compound (27 mg, 59%). 1H NMR (DMSO) δ 8.74(t, 1H), 8.44(dd, 1H), 8.37(m, 2H), 8.31–8.27(m, 3H), 8.12(d, 1H), 7.97(dd, 1H), 7.90(d, 1H), 7.85–7.76(m, 1H), 4.00(m, 2H), 3.79(m, 1H), 3.65(m, 2H), 1.98–1.77(4H, m). MS 510.2 m/z (M−H)−.

Provenance & Evidence