Hydrochloric Acid → HCID 58851318, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-t-butyl-1-(3-(2-(methylamino)-2-oxoethyl)phenyl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea (0.071 g, 0.15 mmol) in THF (2 mL) was added a solution of 1M BH3-THF (1 mL, 1 mmol) at 0° C. under Ar. After stirring the mixtureat 60° C. for 24 h, it was cooled to 0° C., and 3M HCl was added slowly. The mixture was heated to 60° C. for 30 min, cooled to 0° C., and basified with 20% NaOH solution. The product was extracted with CHCl3 (3×25 mL). The combined organic extracts were washed with H2O (1×30 mL), brine, dried (Na2SO4) and concentrated. The resultant residue was dissolved in CH2Cl2 (2 mL) and 3M HCl/EtOAc solution (1 mL) was added and stirred for 10 min to yield (0.025 g, 36%) 1-(3-t-butyl-1-(3-(2-(methylamino)ethyl)phenyl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea as a solid. 1H NMR (300 MHz, DMSO-d6): □ 9.52 (s, 1H), 8.92 (s, 1H), 8.70-8.66 (brs, 2H), 8.05 (dd, J=6.0 Hz, 4.0 Hz, 1H), 7.51-7.42 (m, 3H), 7.34-7.28 (m, 3H), 6.39 (s, 1H), 3.24-3.17 (m, 2H), 3.02-2.98 (m, 2H), 2.58-2.55 (m, 3H), 1.28 (s, 9H). MS (ESI) m/z: 460.2 (M+H+).

Provenance & Evidence