Trifluoroacetic acid → HCID 45377097, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl[3-{[5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thienyl]amino}-3-oxo-2-(phenylmethyl)propyl]carbamate (740 mg, 1.453 mmol) in dichloromethane (7.263 ml) at 25° C. was added TFA (1.119 ml, 14.53 mmol) in one portion. 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-[5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thienyl]-2-(phenylmethyl)propanamide (426 mg, 0.908 mmol, 62.5% yield) as an orange solid: LCMS (ES) m/e 409, 411 (M, M+2)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 12.34 (s, 1 H) 8.06 (br. s., 3 H) 7.68 (s, 1 H) 7.26-7.40 (m, 4 H) 7.24 (d, J=6.82 Hz, 1 H) 6.70 (s, 1 H) 3.94-3.96 (m, 1 H) 3.70 (s, 3 H) 3.14-3.17 (m, 1 H) 3.05 (dd, J=13.52, 6.44 Hz, 2 H) 2.85 (dd, J=14.02, 7.45 Hz, 2 H).

Provenance & Evidence