Tetrahydrofuran → HCID 58920191, compound

Participants

Reaction Steps

1-Cyclopentyl-3-(1-(5-(diphenylmethyleneamino)pyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)urea (77 mg, 0. 12 mmol) was stirred in 2N HCl (1.5 mL) and THF (6 mL) at room temperature for 30 min. LC-MS showed completion of the reaction. EtOAc was added and the solution was washed with saturated NaHCO3, H2O, brine, dried (Na2SO4), filtered, and concentrated to dryness. The residue was purified by flash chromatography (silica gel, hexanes/EtOAc, came out 45-50% EtOAc in hexanes) to give 1-(1-(5-aminopyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-3-cyclopentylurea as colorless film (52 mg, yield: 90.3%). LC-MS ESI 487.32 (M+H) (10-90% MeOH in H2O with 0.1% TFA in a 4-min run, retention time=3.29 min). 1H NMR (400 MHz, CDCl3) δ ppm 1.23-1.32 (m, 1 H), 1.39-1.50 (m, 1 H), 1.58-1.69 (m, 4 H), 1.86 (dt, J=12.47, 6.24 Hz, 1 H), 1.99-2.08 (m, 1 H), 3.54 (d, J=12.47 Hz, 1 H), 3.74 (s, br, 1 H), 3.89-4.00 (m, 1 H), 4.33 (d, J=7.09 Hz, 1 H), 4.44 (d, J=12.47 Hz, 1H), 6.65-6.72 (m, 2 H), 6.88-6.93 (m, 1 H), 6.97-7.02 (m, 1 H), 7.07-7.19 (m, 4 H), 7.22-7.31 (m, 1 H), 7.39 (d, J=10.03 Hz, 1 H), 7.55 (s, 1 H), 7.75 (d, J=2.69 Hz, 1H).

Provenance & Evidence