Triethylamine → HCID 67193759, compound

Participants

Reaction Conditions

Reaction Steps

6-Methoxypyridin-3-ylbenzoic acid (0.7 g, 2.6 mmol) is treated with triethyl amine (0.7 ml, 5 mmol) and TBTU (0.95 g, 3.0 mmol) in DMF (5 ml). 3-(1,2,3,6-Tetrahydropyridin-4-yl)benzonitrile (0.9 g), prepared as above, is added to this suspension and the reaction mixture is heated to 35° C. with stirring for 1.5 h. Solvent is removed, the residue is dissolved in ethyl acetate, and the solution is washed with 1N HCl (2×5 ml). The precipitated solid, 3-{1-[4-(6-methoxypyridin-3-yl)-benzoyl]-1,2,3,6-tetrahydropyridin-4 yl}benzonitrile, is collected (0.60 g); a second crop (0.15 g) is obtained by saturating the organic layer with HCl. 1H NMR (DMSO) δ 8.53 (s, 1H), 8.10 (d, 1H), 7.90 (s, 1H), 7.75 (m, 4H), 4.30 (m, 3H), 6.95 (d, 1H), 6.3 (br, 1H), 4.2 (br, 2H), 3.87 (s, 3H), 3.5 (br, 2H), 2.6 (br, 2H). Ion spray MS M++1: 396.

Provenance & Evidence