1,2-Dichloroethane → 1-(1-Methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Participants

Reaction Steps

1-(1-Methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (150 mg, 0.531 mmol), 3-(aminomethyl)-6-methyl-4-propyl-2(1H)-pyridinone (115 mg, 0.531 mmol), EDC (122 mg, 0.638 mmol), HOAt (72.3 mg, 0.531 mmol), and N-methylmorpholine (0.233 mL, 2.12 mmol) were suspended in DMF (5 mL) and stirred at room temperature overnight. water was added to the reaction mixture, and the contents were filtered. The filter cake was washed with addional water (2×). The crude solid was purified by reverse phase HPLC (mobile phase: 10-30% ACN in H2O, 0.1% TFA). The isolated solid was then neutralized with saturated NaHCO3, and washed with EtOAc (5×15 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound as an off-white solid, 0.060 g (24%). LCMS E-S (M+H)=445.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.84-0.92 (m, 3 H), 1.47-1.54 (m, 2 H), 1.57 (d, J=6.82 Hz, 6 H), 2.14 (s, 3 H), 2.48-2.52 (m, 2 H), 4.42-4.49 (m, 2 H), 5.33-5.43 (m, 1 H), 5.90-5.96 (m, 1 H), 8.28-8.37 (m, 3 H), 8.44-8.48 (m, 1 H), 8.82-8.87 (m, 2 H), 8.99-9.04 (m, 1 H), 11.58 (s, 1 H).

Provenance & Evidence