5-cyanofuran-2-carboxylic Acid → HCID 58638499, compound

Participants

Reaction Steps

4-Methyl-1-(4-methyl-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-6′-yl)-piperazin-2-one (as prepared in the previous step) (99 mg, 0.29 mmol) was converted to corresponding amine according to the procedure in Example 55, step (c) and coupled with 5-cyano-furan-2-carbonyl chloride as prepared in Example 4, step (c) (obtained from 68.5 mg, 0.500 mmol of 5-cyano-furan-2-carboxylic acid as prepared in Example 1) in CH2Cl2 (2 mL) at 0° C. The product was isolated flash chromatography on silica (20% EtOAc/hexane-10% MeOH/EtOAc) to give the title compound (53 mg, 43%). 1H-NMR (CDCl3; 400 MHz): δ 8.98 (br s, 1H), 8.61 (d, 1H, J=8.7 Hz), 7.71 (d, 1H, J=8.7 Hz), 7.28 (d, 1H, J=3.7 Hz), 7.22 (d, 1H, J=3.7 Hz), 3.99 (m, 2H), 3.28 (s, 2H), 3.16 (m, 2H), 2.87-2.77 (m, 4H), 2.38 (s, 3H), 1.83 (m, 2H), 1.62 (m, 1H), 1.44 (m, 2H), 1.04 (d, 3H, J=6.3 Hz). LC-MS (ESI, m/z): Calcd. for C22H26N6O3, 423.2 (M+H), found 423.1

Provenance & Evidence