Tetrahydrofuran → HCID 11497404, compound

Participants

Reaction Steps

To a solution of 1-[2-(4-aminomethyl-phenyl)-5-tert-butyl-2H-pyrazol-3-yl]-3-[4-(pyridin-4-yloxy)phenyl]urea (400 mg, 0.88 mmol) in THF (20 mL) was added N,N-diisopropylethylamine (0.23 mL, 1.31 mmol). A solution of 3-methoxypropionyl chloride (95 mg, 0.88 mmol) in THF (1 mL) was added to the solution at 0° C. under N2 and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was concentrated at reduced pressure and dissolved in EtOAc (100 mL). The solution was washed with water and brine, dried over Na2SO4, and concentrated at reduced pressure. The residue was purified by MPLC (50:50 hexanes/EtOAc) to give 240 mg (52%) of the desired product. 1H-NMR (DMSO-d6) δ 9.16 (s, 1H), 8.42 to 8.40 (m, 4H), 7.50 to 7.37 (m, 6H), 7.08 (d, J=8.7 Hz, 2H), 6.85 (d, J=6.0 Hz, 2H), 6.34 (s, 1H), 4.33 (d, J=6.0 Hz, 2H), 3.86 (s, 2H), 3.26 (s, 3H), 1.25 (s, 9H); MS LC-MS [M+H]+=529, RT=2.29 min.

Provenance & Evidence