HCID 11545711, compound → HCID 11704296, compound

Participants

Reaction Steps

To a solution of 25.3 mg (0.0638 mmol) 5-cyano-furan-2-carboxylic acid (2-piperidin-1-yl-4-thiomorpholin-4-yl-phenyl)-amide (as prepared in Example 6, step (b)) in 2 mL of MeOH-MeCN (1:1) was added 15.0 mg (0.0702 mmol) of sodium periodate in 0.20 mL of water. After stirring for 1.5 h, an additional 4.1 mg (0.019 mmol) of sodium periodate was added. After stirring for 1.5 h, a final 9.5 mg (0.11 mmol) of sodium periodate was added and the mixture stirred for 24 h. The mixture was concentrated to near dryness, extracted with EtOAc (10 mL) and dried (Na2SO4). Concentration and chromatography on a 5-g silica SPE column with a gradient of 60-100% EtOAc-dichloromethane afforded 13.3 mg (51%) of the title compound as a light yellow solid: 1H-NMR (CDCl3; 400 MHz): δ 9.51 (br s, 1H), 8.35 (d, 1H, J=8.9 Hz), ca. 7.2 (d, 1H, obscured by CHCl3 peak), 7.23 (d, 1H, J=3.7 Hz), 6.81 (d, 1H, J=2.6 Hz), 6.77 (dd, 1H, J=8.9, 2.6 Hz), 3.94 (m, 2H), 3.51 (m, 2H), 2.91 (m, 4H), 2.85 (m, 4H), 1.81 (m, 4H), and 1.66 (br m, 2H). Mass spectrum (ESI, m/z): Calcd. for C21H24N4O3S, 413.2 (M+H), found 413.1.

Provenance & Evidence