Acetic Acid → HCID 11996233, compound

Participants

Reaction Conditions

Reaction Steps

A round bottom flask was charged with 6-(aminomethyl)-3-(5-cyclopropyl-1H-pyrazol-3-yl)-N-((S)-1-(4-fluorophenyl)ethyl)-3H-benzo[d]imidazol-5-amine (Example 42; 0.10 g, 0.256 mmol) and acetic acid loaded TFP resin (1.0 mmol/g loading, 0.256 g, 0.256 mmol) in mixture of THF-DCM (1:1, 3 ml) at 0° C. The resulting solution was stirred vigorously at 0° C. for 1 hour and filtered through a Jones tube. The resulting resin was washed with a THF-DCM solution (1:1, 3×5 ml). After removal of solvent, the residue was purified by column chromatography (EtOAc-MeOH=20:1) to give the title compound as an off-white solid (0.083 g, 75%). 1H NMR (400 MHz) 12.67 (s, 1H), 8.50 (m, 1H), 8.18 (s, 1H), 7.39 (m, 3H), 7.11 (m, 2H), 6.73 (s, 1H), 6.09 (d, J=6.0 Hz, 1H), 5.96 (s, 1H), 4.53 (m, 1H), 4.42 (m, 1H), 4.31 (m, 1H), 1.93 (m, 1H), 1.93 (s, 3 h), 1.47 (d, J=6.4 Hz, 3H), 1.02 (m, 2H), 0.76 (m, 2H). MS: Calcd.: 432; Found: [M+H]+ 433.

Provenance & Evidence