Trifluoroacetic acid → HCID 178463564, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-{6-fluoro-2-[(S)-1-(9H-purin-6-ylamino)ethyl]benzoimidazol-1-yl}azetidine-1-carboxylic acid tert-butyl ester (214 mg, 0.47 mmol) in DCM (5 mL) at 0° C. was added TFA (1.7 mL) dropwise. The mixture was stirred at 0° C. for 20 min then slowly warmed to RT. Stirring was continued at RT for 1.5 h. The volatiles were removed under reduced pressure and the resulting residue was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo to afford 378 as a white solid (160 mg, 96%). LCMS (Method K): RT 1.73 min [M+H]+ 353.0. 1H NMR (DMSO-d6, 400 MHz): δ 8.25 (1H, br s), 8.17-8.07 (2H, m), 7.95 (1H, br s), 7.64 (1H, dd, J=8.82, 5.08 Hz), 7.08 (1H, td, J=9.27, 2.42 Hz), 5.80 (1H, br s), 5.63-5.53 (1H, m), 4.14-4.06 (1H, m), 4.01 (2H, d, J=7.20 Hz), 3.93-3.74 (2H, m), 1.63 (3H, d, J=6.71 Hz)

Provenance & Evidence