Trifluoroacetic acid → HCID 45377100, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl (3-{[3,5-dichloro-4-(1-methyl-1H-pyrazol-5-yl)-2-thienyl]amino}-3-oxo-2-phenylpropyl)carbamate (320 mg, 0.646 mmol) in dichloromethane (6.459 ml) at 25° C. was added TFA (0.498 ml, 6.46 mmol). After 30 min, the solution was dry loaded onto silica and neutralized through silica (0-20% MeOH in DCM (1% NH4OH) affording the free base of the title compound. The free base was then dissolved in MeOH (10 mL) and treated with excess 4M HCl in dioxane (2 mL) providing the HCl salt of 3-amino-N-[3,5-dichloro-4-(1-methyl-1H-pyrazol-5-yl)-2-thienyl]-2-phenylpropanamide (188 mg, 0.414 mmol, 64.0% yield) as an orange solid: LCMS (ES) m/e 395, 397 (M, M+2)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 11.65 (s, 1 H) 8.18 (br. s., 3 H) 7.55 (d, J=1.77 Hz, 1 H) 7.28-7.51 (m, 1 H) 7.41 (d, J=5.05 Hz, 4 H) 6.36 (d, J=6.06 Hz, 1 H) 4.53 (dd, J=9.09, 5.31 Hz, 1 H) 3.81 (br. s., 3 H) 3.48-3.59 (m, 1 H) 3.01-3.17 (m, 1 H).

Provenance & Evidence