Trifluoroacetic acid → HCID 178463260, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl ethyl(3-(5-(thiophene-2-carboximidamido)-1H-indol-3-yl)cyclopentyl)carbamate (1.25 g, 2.76 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 reaction then was neutralized with 10% NH4OH solution, the organic layer separated and evaporated. The crude was purified by column chromatography (20% 2N NH3 in MeOH: 80% CH2Cl2) to give the product as a yellow solid (0.87 g, 89%). 1H-NMR (DMSO-d6) δ 1.07 (t, 3H, J=7.2 Hz), 1.45-1.71 (m, 2H), 1.77-2.16 (m, 3H), 2.23-2.40 (m, 1H), 2.64-2.73 (m, 2H), 3.24-3.49 (m, 2H), 6.22 (brs, 2H, NH), 6.63 (d, 1H, J=8.1 Hz), 7.03-7.11 (m, 3H), 7.26 (d, 1H, J=8.4 Hz), 7.58 (d, 1H, J=5.1 Hz), 7.71 (d, 1H, J=3.6 Hz), 10.57 (s, 1H, NH); EI-MS (m/z, %) 352 (M+, 50), 243 (80), 158 (100), EI-HRMS (M+) calc. for C20H24N4S, calculated: 352.1722. found: 352.1725.

Provenance & Evidence