Tetrahydrofuran → HCID 178464308, compound

Participants

Reaction Conditions

Reaction Steps

1.4 mL of diethylcarbonyl chloride and 1.8 mL of N,N-diisopropylethylamine are added to a solution of 0.9 g of intermediate 1 in 30 mL of THF. The reaction mixture is heated at 52° C. for 24 hours. The reaction medium is cooled to ambient temperature and washed with 30 mL of a saturated solution of sodium bicarbonate. The aqueous phase is extracted with three times 30 mL of EtOAc. The organic phases are dried over MgSO4, filtered and concentrated under vacuum in a rotary evaporator. 1.4 g of 3-[3-[6-(3-dimethylaminopropoxy)-5-fluoro-1H-benzimidazol-2-yl]-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]-1,1-diethylurea are obtained in the form of a brown oil. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.22 (t, J=7.5 Hz, 6H); from 1.50 to 2.22 (m, 8H); 2.85 (s, 6H); 3.27 (m, 2H); from 3.31 to 3.48 (m, 4H); 3.67 (m, 1H); 3.97 (m, 1H); 4.17 (t, J=6.0 Hz, 2H); 5.47 (dd, J=2.5 and 10.0 Hz, 1H); 7.22 (d, J=8.0 Hz, 1H); 7.44 (d, J=11.0 Hz, 1H); 8.14 (s, 1H).

Provenance & Evidence