Hydrochloric Acid → HCID 73855138, compound

Participants

Reaction Conditions

Reaction Steps

To an 8 mL vial was added the product of Example 145 (100 mg, 0.15 mmol), anhydrous DMF (5 mL), and tetra-n-butylammonium iodide (570 mg, 1.54 mmol). The solution was heated at 75° C. for 4 h prior to the addition of sodium acetate (250 mg, 3.08 mmol). The reaction solution was then heated 16 h at 75° C. To the solution was added MeOH (2 mL), 5M aqueous NaOH (1 mL) and H2O (1 mL). After heating at 50° C. for 5 h, the reaction mixture was cooled, neutralized with conc HCl and concentrated under reduced pressure. The residue was taken up into DCM (50 mL), and the organic phase was washed with water (2×25 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was chromatographed (SiO2, 0–10% MeOH/DCM) to provide the title compound (5 mg, 5%). 1H NMR (MeOH-d4): δ 8.92 (1H, s), 7.11–7.26 (7H, m), 6.97 (1H, dd), 6.66 (1H, dd), 6.60 (1H, d), 6.44 (1H, d), 5.01 (2H, s), 3.96 (2H, t), 3.77 (2H, t), 3.62 (3H, s), 3.00 (2H, s), 2.82 (2H, q), 2.28 (6H, s), 0.89 (3H, t); MS(ESI) 633(MH+).

Provenance & Evidence