Pivaloyl chloride → HCID 68773954, compound

Participants

Reaction Steps

To a solution of 1-[6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-ylmethyl]-pyrrolidin-3-ylamine hydrochloride (65 mg, 0.161 mmol) in DCM (2 mL) was added DIEA (64 μL, 0.484 mmol) followed by pivaloyl chloride (20 μL, 0.484 mmol) and the resulting solution was stirred (rt, 1 h). The reaction mixture was partitioned with DCM (5 mL) and saturated NaHCO3 (5 mL). The layers were separated and the aqueous layer was extracted with DCM (3×10 mL). The organic layers were combined, dried, filtered and concentrated in vacuo. The resulting residue was purified by flash column chromatography using MeOH:DCM (0-10%) followed by reverse phase HPLC to provide the title compound as a yellow solid (32 mg, 40%). MS (ESI): mass calcd. for C24H26N4O3S, 450.2; m/z found, 451.0 [M+H]+. 1H NMR (500 MHz, CD3OD): 8.48 (dd, J=4.8, 1.3, 1H), 8.30 (dd, J=8.0, 1.6, 2H), 7.72-7.68 (m, 2H), 7.38-7.29 (m, 2H), 6.92 (s, 1H), 4.47-4.37 (m, 1H), 4.13-4.02 (m, 2H), 3.19-3.04 (m, 2H), 2.89-2.75 (m, 2H), 2.38-2.30 (m, 1H), 1.84-1.77 (m, 1H), 1.16 (s, 9H).

Provenance & Evidence