Triethylamine → HCID 59577635, compound

Participants

Reaction Steps

To C-[6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-yl]-methylamine hydrochloride (100 mg, 0.30 mmol) in DCM (3 mL) was added 4-chlorophenylacetyl chloride (57 mg, 0.30 mmol) and Et3N (0.13 mL, 0.90 mmol). The reaction mixture was stirred (rt, 16 h). Another equivalent of 4-chlorophenylacetyl chloride (57 mg, 0.30 mmol) was added, but the reaction remained at 50% conversion. Two equivalents of 4-chlorophenylacetyl chloride (114 mg, 0.60 mmol) and three equivalents of Et3N (0.13 mL, 0.90 mmol) were added. Upon reaction completion, the mixture was washed with sat'd. aq. NaHCO3 and extracted with DCM. After drying and concentration, the residue was purified by reverse phase HPLC to provide the title compound (47 mg, 35%). MS (ESI): mass calcd. for C23H16ClN3O3S, 449.06; m/z found, 449.9 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.56 (dd, J=4.8, 1.6, 1H), 8.04 (dd, J=7.9, 1.6, 1H), 7.60 (d, J=2.0, 1H), 7.58-7.53 (m, 2H), 7.33-7.29 (m, 2H), 7.28-7.24 (m, 1H), 7.24-7.18 (m, 3H), 5.70 (s, 1H), 4.55 (d, J=5.8, 2H), 3.58 (s, 2H).

Provenance & Evidence