Water → HCID 11654827, compound

Participants

Reaction Steps

To a solution of 21.5 mg (0.0542 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 0.6 mL of acetone-water (3:1) was added 22.0 mg (0.163 mmol) of 4-methyl-morpholine N-oxide followed by 25 μL (0.0039 mmol) of a solution of osmium tetroxide (4.0 wt % in water). After stirring for 18 h at RT, 3 mL of water was added and the mixture extracted with EtOAc (2×5 mL). The combined extracts were washed with brine (5 mL), dried (Na2SO4) and concentrated. Chromatography of the resulting residue on a 5-g silica SPE column with 5-6% EtOAc-dichloromethane afforded 19.1 mg (82%) of the title compound as a light yellow solid: 1H-NMR (CDCl3; 400 MHz): δ 9.48 (br s, 1H), 8.36 (d, 1H, J=8.9 Hz), ca. 7.28 (d, 1H, J=3.7 Hz), 7.23 (d, 1H, J=3.7 Hz), 6.77 (d, 1H, J=2.7 Hz), 6.73 (dd, 1H, J=8.9, 2.7 Hz), 3.80 (m, 4H), 3.14 (m, 4H), 2.84 (m, 4H), 1.82 (m, 4H), and 1.67 (br m, 2H). Mass spectrum (ESI, m/z): Calcd. for C21H24N4O4S, 429.2 (M+H), found 429.1.

Provenance & Evidence