Ethanolamine → HCID 86749355, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 529 mg(1.18 mmol) of 3-[trans-3-hydroxy-2,2-dimethyl-4-(1-oxo-1,3-dihydroisoindol-2-yl)-chroman-6-yl]-4-isopropoxy-cyclobut-3-ene- 1,2-dione as prepared in Example 3 in CH3CN (20 mL) and ethanolamine (716 μL; 11.8 mmol) was stirred at room temperature for 4 days. The reaction mixture was heated at 50° C. for 1 h, cooled to room temperature, diluted with H2O, and extracted into 20% THF/CH2Cl2. The organic extracts were dried over MgSO4 and purified by flash chromatography (CH2Cl2 : MeOH :NH4OH (93.25; 4.5; 2.25)) followed by trituration from MeOH/ether to give 124 mg of the title compound as a tan solid, mp 205°-215° C.: 1H-NMR (DMSO-d6 ; 400 MHz) δ8.93 (t, 1 H), 7.79 (dd, 1 H), 7.74 (s, 1 H), 7.69 (dd, 1 H), 7.5-7.64 (m, 3 H), 7.00 (d, 1 H), 5.75 (d, 1 H), 5.2-5.5 (br, 1 H), 4.86 (t, 1 H), 4.4-4.5 (br d, 1 H), 3.67 (m, 2 H), 3.53 (q, 3 H), and 1.27 ppm (s, 3 H); IR (KBr) 1780, 1710, 1660, and 1600 cm-1 ; mass spectrum (+FAB), m/e 449 (M +H), and 471 (M+Na). Anal. Calcd. for C25H24N2O6. 1 H2O C, 64.37; H, 5.62; N, 6.01 Found: C, 64.32; H, 5.83; N, 6.18.

Provenance & Evidence