Diisopropylethylamine → 3-[4-(5-Phenylethyl-pyridine-3-carbonyl)-piperazin-1-yl]-benzonitrile

A solution of 5-phenylethynyl-pyridine-3-carboxylic acid (0.4 g, 1.8 mmol) in anhydrous dimethylformamide (3 ml) is treated with HATU (0.7 g, 1.8 mmol) and diisopropylethylamine (0.6 ml, 3.3 mmol). The reaction mixture is stirred 10 mins. at ambient temperature before being treated with a solution of 1-(3-cyanophenyl)piperazine (0.3 g, 1.6 mmol) in dimethylformamide (5 ml). The reaction mixture is stirred at ambient temperature for 18 hours, concentrated under vacuum and the residue partitioned between dichloromethane (2×40 ml) and saturated aqueous sodium bicarbonate (40 ml). The organic layer is dried (magnesium sulfate), concentrated under vacuum and the residue chromatographed on silica gel (ethyl acetate) to give the title compound as a yellow oil (0.33 g). 1H NMR (CDCl3, 500 MHz) δ8.82 (s, 1H), 8.61 (s, 1H), 7.90 (s, 1H), 7.58 (m, 2H), 7.39 (m, 4H), 7.16 (m, 3H), 3.95 (br m, 2H), 3.63 (br m, 2H), 3.30 (br m, 4H), EI MS M++H: 393.

1. stirringThe reaction mixture is stirred at ambient temperature for 18 hours
2. concentrationconcentrated under vacuum
3. customthe residue partitioned between dichloromethane (2×40 ml) and saturated aqueous sodium bicarbonate (40 ml)
4. dry with materialThe organic layer is dried (magnesium sulfate)
5. concentrationconcentrated under vacuum
6. customthe residue chromatographed on silica gel (ethyl acetate)

ORD-Eintrag

ord-ac3ec2b55b6a4f5bb096505160cd6c1c

Quelldatensatz

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07947684B2