Trifluoroacetic acid → HCID 68924273, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl ethyl(3-(5-(thiophene-2-carboximidamido)-1H-indol-3-yl)cyclohexyl)carbamate (0.75 g, 1.61 mmol) was treated with 20% 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 solution, 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 (0.50 g, 85%). 1H-NMR (DMSO-d6) δ 1.05 (t, 3H, J=6.9 Hz), 1.44-1.51 (m, 3H), 1.58-1.82 (m, 3H), 1.89-1.97 (m, 2H), 2.58 (q, 2H, J=7.2 Hz), 2.85-2.99 (m, 1H), 3.08-3.23 (m, 1H), 6.19 (s, 2H), 6.62 (d, 1H, J=8.4 Hz), 6.98-7.00 (m, 2H), 7.09 (dd, 1H, J=3.9, 5.1 Hz), 7.26 (d, 1H, J=8.4 Hz), 7.58 (d, 1H, J=5.1 Hz), 7.70 (d, 1H, J=3.0 Hz), 10.54 (s, 1H); ESI-MS (m/z, %) 367 (MH+, 50%), 322 (100), ESI-HRMS (MH+) calc. for C21H27N4S, calculated: 367.1950. found: 367.1956.

Provenance & Evidence