Hydrochloric Acid → HCID 21083985, compound

Participants

Reaction Steps

To a solution of the compound of Example 112 (310 mg, 0.61 mmol) in dioxane (35 mL) was added 4M HCl(aq) (20 mL) and the mixture heated at reflux for 18 h. Reaction had not reached completion and so a few drops of concentratedHCI were added and reflux continued for 5 h. The reaction was quenched with saturated Na2CO3(aq) and extracted with DCM (×3). The combined DCM extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude product contained a small amount of residual ester starting material. The product was therefore dissolved in EtOH (15 mL) and heated at reflux with NaOH (50 mg) for 16 h. Solvent was removed in vacuo and the residue partitioned between DCM and saturated Na2CO3(aq). The DCM layer was washed with Na2CO3(aq) (×3), dried (Na2SO4) and concentrated in vacuo to give the pure title compound as an off-white solid (280 mg). δH (DMSO-d6) 8.10–7.95 (2H, m), 7.86 (1H, dt, J 9.5, 2.6 Hz), 7.74–7.63 (4H, m), 7.55–7.52 (2H, m), 6.92 (1H, d, J 9.5 Hz), 3.72–3.67 (8H, m), 2.67 (3H,s). LCMS (ES+) RT 2.47 minutes, 438 (M+H)+.

Provenance & Evidence