Morpholine → HCID 49833716, compound

Participants

Reaction Steps

To a solution 2-(2-chloromethyl-benzofuran-6-yloxy)-thiazolo[4,5-b]pyridine (110 mg, 0.3 mmol) in MeCN (3 mL) was added DIEA (209 μL, 0.155 mg, 0.8 mmol) followed by morpholine (27 μL, 27 mg, 0.3 mmol) and stirred (rt, 12 h). The reaction mixture was partitioned between DCM (15 mL) and saturated NaHCO3 (5 mL). The organic layer was washed with saturated NH4Cl (10 mL), dried, filtered and concentrated in vacuo. The resulting residue was purified by reverse phase chromatography to provide the title compound as colorless crystals (41 mg, 37%). MS (ESI): mass calcd. for C19H17N3O3S, 367.1; m/z found, 368.1.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.56 (dd, J=4.8, 1.7, 1H), 8.01 (dd, J=7.9, 1.7, 1H), 7.59-7.51 (m, 2H), 7.28-7.25 (m, 1H), 7.20 (dd, J=8.0, 4.8, 1H), 6.65 (s, 1H), 3.75 (dd, J=15.5, 10.8, 4H), 3.70 (s, 2H), 2.62-2.49 (m, 4H).

Provenance & Evidence