1,2-Dichloroethane → HCID 53629034, compound

Participants

Reaction Steps

(3-Chloropyrazin-2-yl)(2-phenylquinolin-7-yl)-methanamine (120.00 mg, 0.35 mmol), EDC (100.64 mg, 0.53 mmol) and HOBt (47.29 mg, 0.35 mmol) were suspended in CH2Cl2 (2 mL) and charge with DIEA (122.00 μL, 0.70 mmol) followed by the addition of 1-N-Cbz-4-piperidineacetic acid (127.56 mg, 0.46 mmol). The reaction mixture was stirred at rt for 16 h. The reaction mixture was diluted with CH2Cl2 (10 mL) and washed with saturated NaHCO3 (2×20 mL) and brine (2×20 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by a 10 g Jones silica gel (wetted with 50% EtOAc/Hexane, dried loaded onto silica, and run with 60% EtOAc/Hexanes→70% EtOAc/Hexanes) affording the desired product; 1H NMR (400 MHz, CHLOROFORM-d) δ 8.56 (1 H, d, J=2.47), 8.39 (1 H, d, J=2.50), 8.23 (1 H, d, J=4.77), 8.11 (2 H, d, J=7.06), 7.85 (3 H, dd, J=8.60, J=8.38), 7.74 (1 H, s), 7.50 (3 H, m), 7.32 (6H, m), 6.78 (1 H, d, J=7.76), 5.10 (2 H, s), 4.11 (2 H, m), 2.75 (2 H, m), 2.21 (2 H, d, J=7.00), 2.01 (1 H, m), 1.67 (2 H, m), 1.15 (2 H, d, J=8.921); MS (ES+): m/z 605.96/606.98/608.93 (100/40/15) [MH+]; HPLC: tR=3.33 min. (OpenLynx, nonpolar—5 min.).

Provenance & Evidence