1-(1-Phenylethyl)piperazine → 2-chloro-N,N-dimethyl-5-(4-(4-(1-phenylethyl)-1-piperazinyl)-6-quinolinyl)-3-pyridinamine

Participants

Reaction Conditions

Reaction Steps

(Some starting materials may be obtained from Chess GmbH, Mannnheim, Germany) To a microwave vial (5 mL), 2-chloro-5-(4-chloroquinolin-6-yl)-N,N-dimethylpyridin-3-amine (0.0846 g, 0.266 mmol) and 1-(1-phenylethyl)-piperazine (0.125 mL, 0.665 mmol) were added into DMSO (4 mL). The mixture was stirred at 90 oC for 2.5 h, at 110° C. for 3 h, then at RT for overnight. The reaction was partitioned between water (20 mL) and EtOAc (20 mL). The aqueous phase was extracted with EtOAc (2×20 mL). The combined organic phases were washed with saturated aqueous NaCl (40 mL). The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (eluent: acetone in hexanes 0% -50%) to afford the title compound as a white solid (0.0886 g). m/z: calc'd for C28H30ClN5; 471.2, found: 472.2 (M+1). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.46 (d, J=6.6 Hz, 3 H), 2.63-2.89 (m, 4 H), 2.94 (s, 6 H), 3.29 (t, J=4.4 Hz, 4 H), 3.51 (d, J=6.7 Hz, 1 H), 6.88 (d, J=5.0 Hz, 1 H), 7.28-7.42 (m, 5 H), 7.56 (d, J=2.2 Hz, 1 H), 7.84 (dd, J=8.7, 2.1 Hz, 1 H), 8.10-8.20 (m, 2 H), 8.33 (d, J=2.2 Hz, 1 H), 8.75 (d, J=5.0 Hz, 1 H).

Provenance & Evidence