Trifluoroacetic acid → HCID 178482138, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl methyl(3-(5-(thiophene-2-carboximidamido)-1H-indol-3-yl)cyclohexyl)carbamate (0.60 g, 0.13 mmol) was treated with 20% TFA solution (31 mL) in dichloromethane at 0° C. and the mixture left to stir for 2 hours at 0° C. The solution then was neutralized with 10% NH4OH, the organic layer separated and evaporated. The crude product was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:4) to give the final product as a yellow solid (0.45 g, quantitative). 1H-NMR (DMSO-d6) δ 1.51-1.60 (m, 3H), 1.69-1.77 (m, 3H), 1.83-1.91 (m, 1H), 1.96-2.07 (m, 1H), 2.40 (s, 3H), 3.24-3.51 (m, 3H), 6.20 (brs, 2H, NH), 6.63 (d, 1H, J=10.2 Hz), 7.02 (d, 2H, J=10.4 Hz), 7.09 (dd, 1H, J=3.6, 4.8 Hz), 7.58 (d, 1H, J=5.1 Hz), 7.71 (d, 1H, J=3.3 Hz), 10.59 (s, 1H, NH); ESI-MS (m/z, %) 353 (MH+, 80), 322 (100), ESI-HRMS (MH+) calc. for C20H25N4S (MH+), calculated: 353.1794. found: 353.1812.

Provenance & Evidence