1,1'-Carbonyldiimidazole → HCID 86703664, compound

Participants

Reaction Steps

To a solution of 5-chloro-4-(cyclohexyloxymethyl)-2-fluorobenzoic acid (0.12 g, 0.42 mmol) in anhydrous tetrahydrofuran (5 mL) was added 1,1′-carbonyldiimidazole (0.088 g, 0.55 mmol). The reaction solution was heated to reflux under a nitrogen atmosphere for 15 minutes and cooled to ambient temperature. To this solution was added azetidine-1-sulfonamide (0.086 g, 63 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.16 g, 1.05 mmol). The mixture was stirred at ambient temperature for 16 hours, then diluted with ethyl acetate (15 mL) and washed with 1 M hydrochloric acid (2×10 mL) and brine (2×10 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by reverse-phase preparative HPLC to afford the title compound (0.005 g, 3%) as a colorless powder: MS (ES+) m/z 405.1, 407.1 (M+H)

Provenance & Evidence