Hydrochloric Acid → HCID 59577737, compound

Participants

Reaction Steps

To a solution 1-[6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-ylmethyl]-piperidine-4-carboxylic acid ethyl ester (77 mg, 0.18 mmol) in IPA (1.7 mL) was added 2 M KOH (0.9 mL, 1.8 mmol) and stirred (rt, 2 h). The pH of the reaction mixture was adjusted to pH 8 with 1 M HCl (1.7 mL) and partitioned with DCM (30 mL). The aqueous phase was extracted with DCM (3×30 mL). The organic layers were combined, dried, filtered and concentrated in vacuo to provide the title compound as a yellow solid (28 mg, 39%). MS (ESI): mass calcd. for C21H19N3O4S, 409.1; m/z found, 410.0 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.49 (dd, J=4.8, 1.4, 1H), 8.31 (dd, J=8.0, 1.5, 1H), 7.98 (5, 1H), 7.89 (d, J=8.6, 1H), 7.75-7.70 (m, 1H), 7.44-7.29 (m, 2H), 4.06 (5, 2H), 3.28-3.08 (m, 2H), 2.72-2.47 (m, 2H), 2.34-2.22 (m, 1H), 2.09-1.95 (m, 2H), 1.93-1.72 (m, 2H). The remaining proton was not detected (COOH).

Provenance & Evidence