Triethylamine → (E)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-3-[5-(4-methylphenyl)furan-2-yl]acrylic amide

Participants

Reaction Steps

To a solution of (E)-3-[5—(4-methylphenyl)furan-2-yl]acrylic acid (200 mg), 4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]aniline (212 mg) and triethylamine (0.15 ml) in DMF (10 ml) was added diethyl cyanophosphate (0.16 ml) at 0° C., and the mixture was stirred at room temperature for 3 hours. To the mixture was added ethyl acetate; and the mixture was washed with water and saturated sodiumlchloride solution, dried with magnesium sulfate and concentrated. The residue was separated and purified with column chromatography (ethanol/ethyl acetate=1:50→1:25→1:10) to give (E)-N-[4-[N-methyl-N-(tetrahydropyran-4-yl)aminomethyl]phenyl]-3-[5—(4-methylphenyl)furan-2-yl]acrylic amide (Compound 210) (87 mg) as brown amorphous. 1H-NMR (200 MHz, CDCl3) δ 1.53-1.85 (4H, m), 2.21 (3H, s), 2.38(3H, s), 2.54-2.72 (1H, m), 3.31-3.44 (2H, m), 3.56 (2H, s), 3.98-4.11 (2H, m), 6.52 (1H, d, J=15.4 Hz), 6.67-6.69 (2H, m), 7.22 (2H, d, J=8.0 Hz), 7.29 (2H, d, J=8.4 Hz), 7.41 (1H, s), 7.48-7.64 (5H, m).

Provenance & Evidence