Diisopropylcarbodiimide → (S)-2-(1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-ylamino)-N-(1-phenylethyl)acetamide

Participants

Reaction Steps

A solution of 2-(1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-ylamino) acetic acid (0.035 g, 0.095 mmol), DIC (0.018 g, 0.143 mmol) and HOBt (0.020 g, 0.143 mmol) in THF (5 ml) was stirred at rt for 10 min. (S)-(−)-α-methyl benzyl amine (0.013 g, 0.104 mmol) was added to the reaction mixture dropwise at rt and stirring was continued for 16 h. The reaction mixture was poured into ice cold water and the precipitated product was collected by filtration and dried under vacuum. The crude product was purified by preparative HPLC using acetonitrile/water as mobile phase to yield the title compound as a white solid (0.018 g, 42%). [1H-NMR (CDCl3, 300 MHz) δ 7.52-7.38 (m, 4H), 7.32-7.21 (m, 6H), 6.66 (s, 1H), 6.39 (d, 1H), 5.51 (t, 1H), 5.30-5.15 (m, 1H), 4.20 (dd, 2H), 3.95 (s, 3H), 1.52 (d, 3H); HPLC RtA=5.294 (98%) min; LCMS RtA=1.682 min; [M+H]+=454.1]

Provenance & Evidence