Acetic Acid → HCID 60207451, compound

Participants

Reaction Steps

To a solution of 5-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(3-oxopropyl)thiophene-2-carboxamide (0.13 g, 0.32 mmol) and 3-hydroxy-piperidine (89.0 mg, 0.38 mmol) in tetrahydrofuran (3.0 mL) under nitrogen, was added acetic acid (0.2 mL). The resulting mixture was stirred at ambient temperature for 30 minutes. Then sodium triacetoxyboronhydride was added and the reaction mixture was stirred at ambient temperature for additional 4 hours. After this time, the reaction mixture was diluted with water and extracted with ethylacetate. The organic layer was separated, dried (Na2SO4) and concentrated. The crude residue was purified by silica gel chromatography using a 90:10 mixture of dichloromethane and methanol as eluent to afford the title product as a solid (14.0 mg, 37% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.99 (2H, m), 8.83 (1H, m), 8.41 (1H, s), 4.58 (1H, m), 3.19 (2H, m), 2.80 (1H, m), 2.61 (1H, m), 2.27 (2H, m), 1.76 (2H, m), 1.61 (3H, m), 1.38 (1H, m), 1.23 (1H, m), 1.06 (1H, m). MS m/z: 491.11, 493.13 [M+H]+.

Provenance & Evidence