Pyridine → 1-(1-Benzyl-pyrrolidin-3-yl)-3-(3-methyl-isoquinolin-5-yl)urea

Participants

Reaction Steps

To a stirred solution of (D2) (1.50 g, 10.30 mmol) and pyridine (0.91 mL,1 1.30 mmol) in dichloromethane (50 mL) was added phenylchloroformate (1.42 mL, 11.30 mmol) dropwise at 25° C. over 10 min. After 1 h, triethylamine (1.58 mL, 11.30 mmol) was added and the reaction left to stir for a further 20 min. After this period, (R)—N-benzyl-3-aminopyrrolidine (1.67 g, 10.30 mmol) was added in dichloromethane (50 mL) and the whole stirred at 25° C. for 18 h. The mixture was then diluted with dichloromethane (100 mL), washed with water (100 ml) and dried (Na2SO4). Evaporation in vacuo gave a solid, which on recrystallisation from dichloromethane/petroleum ether gave the title compound as a pale brown solid (2.56 g). 1H NMR (CDCl3)  : 2.20-2.40 (3H, m), 2.45-2.50 (1H, m), 2.63 (3H, s), 2.70-2.80 (1H, m), 2.90-3.00 (1H, m), 3.50-3.60 (2H, m), 4.25-4.35 (1H, m), 5.35 (1H, d, J=8.1 Hz), 7.15-7.20 (2H, m), 7.25-7.30 (3H, m), 7.45-7.55 (2H, m), 7.77 (2H, d, J=7.3 Hz), 9.17 (1H, s).

Provenance & Evidence