Dimethylformamide → (S)-2-amino-N-(4-(3-(piperidin-4-yloxy)phenyl)but-3-ynyl)pent-4-ynamide

Participants

Reaction Steps

5-(Biphenyl-3-yl)pent-4-yn-1-amine (0.040 g, 0.17 mmol), 2-tert-Butoxycarbonylamino-pent-4-ynoic acid (40 mg, 0.19 mmol), HOBt (28 mg, 0.21 mmol), EDCl (40 mg, 0.21 mmol), and DIEA (0.044 mL, 0.25 mmol) were taken into DMF (3 mL) and stirred at room temperature overnight. The reaction was then quenched with water and the resulting mixture extracted with EtOAc. The organic layer was washed with saturated NaHCO3 and brine, then dried over sodium sulfate and the solvent removed in vacuo. The resulting residue was taken up into DCM/TFA (4/1, 5 mL) and the resulting mixture was stirred at room temp for 1 hr. The solvent was removed in vacuo and prepped on the Gilson HPLC to yield the title compound, as its corresponding TFA salt. MH+ 331.2; 1H NMR (300 MHz, DMSO): δ 1.6-1.8 (m, 3H), 2.45 (m, 2H), 2.7 (s, 2H), 3.2-3.4 (m, 2H), 3.9 (s, 1H), 7.3-7.4 (m, 5H), 7.6-7.7 (m, 4H), 8.3 (s, 2H), 8.6 (s, 1H)

Provenance & Evidence