Triethylamine → HCID 67270810, compound

Participants

Reaction Steps

To a solution of 1-(2-(4-(t-butoxycarbonyl)piperazin-1-yl)quinolin-6-yl)-3-t-butyl-1H-pyrazole-5-carboxylic acid (0.1 g, 0.21 mmol) in toluene (2 mL) was added Et3N (0.032 mL, 0.23 mmol) and 2,3-dichloroaniline (84 mg, 0.52 mmol). The reaction mixture was stirred at RT and DPPA (63 mg, 0.23 mmol) was added. The reaction mixture was heated at 100° C. for 2 h, cooled, quenched with H2O, and extracted with EtOAc (3×50 mL). The organic extracts were washed with brine, dried (Na2SO4), concentrated and purified by column chromatography to yield t-butyl 4-(6-(3-t-butyl-5-(3-(2,3-dichlorophenyl)ureido)-1H-pyrazol-1-yl)quinolin-2-yl)piperazine-1-carboxylate (0.11 g, 83% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.26 (s, 1H), 8.77 (s, 1H), 8.17 (d, J=9.6 Hz, 1H), 8.07 (dd, J=3.2, and 6.8 Hz, 1H), 7.87 (d, J=2.0 Hz, 1H), 7.68 (m, 2H), 7.31 (m, 3H), 6.42 (s, 1H), 3.74 (m, 4H), 3.47 (m, 4H), 1.44 (s, 9H), 1.30 (s, 9H); LC-MS (EI) m/z: 638.3 (M+H+).

Provenance & Evidence