Trifluoroacetic acid → HCID 11619776, compound

Participants

Reaction Steps

The procedure of Example 17 was followed using 40.0 mg (0.0546 mmol) of 5-cyano-furan-2-carboxylic acid [2-(4-methyl-piperidin-1-yl)-4-piperazin-1-yl-phenyl]-amide tris(trifluoroacetic acid salt) (as prepared in Example 16), 7.6 μL (0.0655 mmol) of is methanesulfonyl chloride and 47.6 μL (0.716 mmol) of DIEA. Chromatography on a 2-g silica SPE column with 5-10% EtOAc-dichloromethane followed by concentration from EtOAc-hexane (1:1, 2 mL) afforded 23.3 mg (91%) of the title compound as a crystalline yellow solid: 1H-NMR (CDCl3; 400 MHz): δ 9.59 (br s, 1H), 8.33 (d, 1H, J=8.8 Hz), 7.22, 7.25 (AB q, 2H, J=3.7 Hz, partially obscured by CHCl3 peak), 6.79 (d, 1H, J=2.7 Hz), 6.73 (dd, 1H, J=8.8, 2.7 Hz), 3.39-3.41 (m, 4H), 3.25-3.27 (m, 4H), 2.98-3.01 (m, 2H), 2.84 (s, 3H), 2.70-2.76 (m, 2H), 1.83-1.87 (m, 2H), 1.50-1.65 (m, 1H), 1.42-1.58 (m, 2H) and 1.08 (d, 3H, J=6.2 Hz). Mass spectrum (ESI, m/z): Calcd. for C23H29N5O4S, 472.2 (M+H), found 472.2.

Provenance & Evidence