Trifluoroacetic acid → HCID 70913262, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl N-{4-[(5-chloro-3-{[(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]carbamoyl}-2-ethylphenyl)(ethyl)amino]cyclohexyl}carbamate (100 mg, 0.18 mmol) in CH2Cl2 (4.0 ml) at 0° C., was added trifluoroacetic acid (1.0 ml). The reaction mixture was stirred at 0° C. for 40 minutes and then stirred for 2 hours at room temperature. The reaction mixture was concentrated in-vacuo and the residue was basified with a saturated solution of NaHCO3 (aq) (10 ml) until the pH was 8. The aqueous residue was extracted with 20% MeOH/CH2Cl2 (4×15 ml). The combined organic layers were dried (MgSO4), filtered and concentrated in-vacuo to give the title compound (108 mg, 113%) as a yellow solid. LC-MS 48%, 2.88 min (7 minute LC-MS method), m/z=459.1 and 39%, 2.96 min (7 minute LC-MS method), m/z=459.1. 1H NMR shows a mixture of cis/trans isomers.

Provenance & Evidence