Acetic Acid → HCID 58873186, compound

Participants

Reaction Steps

Prepare with procedure described in literature Sznaidman M. L.; Meade E. A.; Beauchamp, L. M.; Russell, R.; Tisdale, M., Bioorg. Med. Chem. Lett., 1996, 6, 5, 565-568. Stir at room temperature under nitrogen a mixture of 3-[4-(3-amino-thiophen-2-yl)-phenyl]-4-cyano-5-ethyl-thiophene-2-carboxylic acid ethyl ester (0.05 g, 0.131 mmol), paraformaldehyde (0.041 g, 1.31 mmol), sodium cyanoborohydride (0.026 g, 0.393 mmol) and acetic acid (0.02 mL, 0.262 mmol) in dry acetonitrile (1 mL). After 3 h add water and extract with ethyl acetate. Combine the organic layers, dry over sodium sulfate, filter and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography (silica gel) eluting with ethyl acetate:hexane 1:2 to provide the title compound (0.033 g, 61%). Mass spectrum (m/e): 411 (M+1). 1H-NMR (CDCl3) δ1.19 (t, 3H, J=7.2 Hz); 1.44 (t, 3H, J=7.5 Hz); 2.71 (s, 6H); 3.09 (c, 2H, J=7.5 Hz); 4.20 (c, 2H, J=7.2 Hz); 6.97 (d, 1H, J=5.4 Hz); 7.19 (d, 1H, J=5.6 Hz); 7.38-7.43 (m, 2H); 7.81-7.86 (m, 2H).

Provenance & Evidence