Trifluoroacetic acid → HCID 178482138, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl methyl(3-(5-(thiophene-2-carboximidamido)-1H-indol-3-yl)cyclohexyl)carbamate (0.30 g, 0.66 mmol) was treated with 20% trifluoroacetic acid (TFA) solution (31 mL) in dichloromethane at 0° C. and the mixture left to stir for 2 h at 0° C. The solution then was neutralized with 10% NH4OH, the organic layer separated and evaporated. The crude was purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:4) to give the title product as a yellow solid (0.22 g, quantitative). 1H-NMR (DMSO-d6) δ 1.28-1.61 (m, 4H), 1.84-2.01 (m, 2H), 2.08-2.11 (m, 1H), 2.27-2.35 (m, 1H), 2.58 (s, 3H), 2.86-2.94 (m, 1H), 3.08-3.25 (m, 1H), 7.10 (d, 1H, J=8.4 Hz), 7.28 (d, 1H, J=2.1 Hz), 7.39 (pseudo t, 1H, J=4.5 Hz), 7.52 (d, 1H, J=8.4 Hz), 7.65 (s, 1H), 8.12 (d, 1H, J=3.6 Hz), 8.16 (d, 1H, J=4.5 Hz), 8.58 (s, 2H, NH), 9.61 (s, 1H); ESI-MS (m/z, %) 353 (100), ESI-HRMS calc. for C20H25N4S 353.1794 found 353.1792.

Provenance & Evidence