Trifluoroacetic acid → 5-Methylsulfanyl-4-[3'-(2,2,2-trifluoro-acetyl)-biphenyl-3-sulfonyl]-thiophene-2-carboxamidine trifluoroacetate

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Reaction Steps

(Imino-{5-methylsulfanyl-4-[3′-(2,2,2-trifluoro-acetyl)-biphenyl-3-sulfonyl]-thiophen-2-yl}-methyl)-carbamic acid tert-butyl ester (30 mg, 0.051 mmol, as prepared in Example 29, step a) was treated with trifluoroacetic acid (50% in DCM) for 1 hr at rt. The reaction mixture was concentrated in vacuo and the residue obtained was purified using C18-HPLC (20–60% CH3CN in H2O (0.1% TFA) over 25 min) to give 20 mg (80%) of the title compound as a white solid. 1H-NMR (CD3OD; 400 MHz) δ 8.35 (s, 1H), 8.33 (t, 1H, J=1.7 Hz), 7.98–8.07 (m, 2H), 7.90–7.93 (m, 1H), 7.68–7.78 (m, 3H), 7.60 (t, 1H, J=7.8 Hz), 2.77 (s, 3H). 19F-NMR (CDCl3; 400 MHz) δ −84.99 (s). ESI-MS (m/z): Calcd. for C20H15F3N2O3S3: 485.5 (M+H); found: 485.3, 503.3 (M+H2O), 517.3 (M+CH3OH).

Provenance & Evidence