Sulfuric Acid → HCID 86707768, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-bromo-5-[(4-chloro-phenyl)-hydroxy-methyl]-1-cyclobutyl-1H-imidazole-4-carboxylic acid (3-chloro-4-fluoro-phenyl)-amide (step AK1; 0.470 g, 0.907 mmol) and AcOH (4.53 ml) was added H2SO4 98% (0.592 ml, 10.88 mmol). The solution was stirred for 7 h at 110° C. The reaction mixture was concentrated in vacuo. The residue was neutralized with 1M NaHCO3 and extracted with EtOAc (2×). The organic phases were washed with brine and dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (hexane/EtOAc, 1:1), then triturated in diisopropyl ether/hexane to afford the title compound. tR: 1.29 min (LC-MS 2); ESI-MS: 496.0 [M+H]+ (LC-MS 2); 1H-NMR (DMSO-d6, 400 MHz) δ ppm 7.79 (m, 1H), 7.49 (m, 1H), 7.38 (s, 4H), 7.35 (m, 1H), 6.89 (s, 1H), 4.73 (m, 1H), 2.45 (m, 2H), 1.86 (m, 1H), 1.63 (m, 1H), 1.42 (m, 2H).

Provenance & Evidence