Trifluoroacetic acid → 5-(3-Aminoprop-1-ynyl)-3-benzothiazol-2-ylpyridin-2-ylamine

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Reaction Steps

To a solution of [3-(6-amino-5-benzothiazol-2-ylpyridin-3-yl)-prop-2-ynyl]-carbamic acid tert-butyl ester (0.225 g, 0.6 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (0.5 mL, 6 mmol), the mixture was stirred at RT for 2 h. Aq. satd. NaHCO3 (20 mL) was added, and the mixture was extracted with CH2Cl2/MeOH (10%, 4×30 mL). The organic extracts were dried over Na2SO4, filtered, and concentrated at reduced pressure to give the title compound. 1H NMR (CDCl3, 300 MHz): δ=3.78 (s, 2H), 7.42-7.58 (m, 2H), 7.88 (d, J=6.8 Hz, 1H), 8.05-8.07 (m, 2H), 8.32 (d, J=1.8 Hz, 1H). MS (ES+): m/z=281.14 (100) [MH+]. HPLC: tR=2.01 min (ZQ2, polar—5 min).

Provenance & Evidence