Trifluoroacetic acid → HCID 66745103, compound

Participants

Reaction Steps

To a solution of tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-[4-(propanoylamino)cyclohexen-1-yl]pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (21 mg, 0.03 mmol) in DCM (220 μL) was added TFA (326 mg, 220 μL, 2.9 mmol) and the reaction mixture was stirred for 40 minutes at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DMF (1 mL) and purified by Gilson reverse phase HPLC using (5-99% ACN/H2O (5 mM HCl)) to yield N-(4-(5-Amino-6-(5-(4-((methylamino)methyl)phenyl)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)cyclohex-3-enyl)propionamide. 1H NMR (400 MHz, MeOD) d 8.41 (s, 1H), 8.31 (d, J=8.4 Hz, 2H), 7.77 (d, J=8.3 Hz, 2H), 6.64 (s, 1H), 4.34 (s, 2H), 4.11-3.98 (m, 1H), 2.81 (s, 4H), 2.63 (d, J=17.8 Hz, 2H), 2.26 (q, J=7.7 Hz, 3H), 2.15-2.04 (m, 1H), 1.78 (dd, J=11.3, 5.0 Hz, 1H), 1.18 (t, J=7.6 Hz, 3H). LC/MS m/z 434.2 [M+H]+.

Provenance & Evidence