Hydrochloric Acid → HCID 86703750, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-chloro-4-((2,6-dimethylcyclohexyl)methoxy)-2-fluorobenzoic acid (0.07 g, 0.22 mmol) in tetrahydrofuran (2 mL) under an atmosphere of nitrogen was added carbonyldiimidazole (0.053 g, 0.33 mmol). The reaction mixture was stirred at 70° C. for 1 hour. The mixture was cooled to room temperature and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.07 mL, 0.45 mmol) was added followed by cyclopropanesulfonamide (0.045 mg, 0.374 mmol). Stirring continued at room temperature for 18 hours. 5% aqueous hydrochloric acid solution (0.15 mL) was added and the mixture was concentrated and directly purified by column chromatography (0 to 30% ethyl acetate in hexanes) to afford the title compound (0.026 g, 28%) as a colorless solid: 1H NMR (300 MHz, DMSO-d6) δ 12.09-11.90 (m, 1H), 7.71 (d, J=7.07 Hz, 1H), 7.35 (d, J=12.32 Hz, 1H), 4.12-4.06 (m, 2H), 3.11-2.96 (m, 1H), 1.98-0.80 (m, 19H); MS (ES−) m/z 416.2, 418.2 (M−1).

Provenance & Evidence