1,1'-Carbonyldiimidazole → HCID 25000363, compound

Participants

Reaction Conditions

Reaction Steps

A solution of compound C (133 mg, 0.56 mmol) and CDI (91 mg, 0.56 mmol) in anhydrous acetonitrile (1.0 mL) was stirred for 1 hour at ambient temperature. 2-Amino-6-methyl-benzoic acid (41 mg, 0.27 mmol) was added, and the mixture was stirred at 60° C. overnight. The reaction solution was diluted with water (2 mL) and DMF (2 mL), filtered, then purified by C18 reverse phase chromatography to afford compound 46 as an off-white powder (11 mg, 35% yield). 1H-NMR δ (CDCl3): 8.32 (dd, 1H, J=4.8 Hz, J=2.0 Hz), 8.09 (dd, 1H, J=8.0 Hz, J=1.6 Hz), 7.68 (t, 1H, J=15.6 Hz, J=0.8 Hz), 7.52 (t, 1H, J=4.0 Hz, J=7.6 Hz), 7.33 (d, 1H, J=7.2 Hz), 6.82 (dd, 1H, J=8 Hz, J=4.8 Hz), 3.95 (br s, 1H), 3.81 (br s, 1H), 3.57-3.64 (m, 2H), 3.48-3.53 (m, 2H), 2.83 (s, 3H), 2.64 (br s, 6H), 2.30 (br s, 1H). ESMS: 351.1 [M+H]+.

Provenance & Evidence