1,2-Dichloroethane → HCID 56597704, compound

Participants

Reaction Steps

1-(1-Methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (100 mg, 0.354 mmol), 3-(aminomethyl)-4-cyclopropyl-6-methyl-2(1H)-pyridinone (104 mg, 0.354 mmol), EDC (81 mg, 0.425 mmol), HOAt (48 mg, 0.354 mmol), and N-methylmorpholine (0.156 mL, 1.42 mmol) were suspended in DMF (5 mL) and stirred at room temperature overnight. The contents were filtered, washed with ethanol, and then concentrated in vacuo. The crude solid was purified by reverse phase HPLC (mobile phase: 20-40%, ACN in H2O, 0.1% TFA). The isolated solid was then neutralized with saturated NaHCO3, and washed with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound as an off-white solid, 0.042 g (26%). LCMS E-S (M+H)=443.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.71-0.78 (m, 2H), 0.94 (dd, J=8.34, 2.27 Hz, 2H), 1.57 (d, J=6.57 Hz, 6H), 2.12 (s, 3H), 2.13-2.18 (m, 1H), 4.62 (d, J=4.80 Hz, 2H), 5.38 (s, 1H), 5.54 (s, 1H), 8.37 (s, 1H), 8.44-8.54 (m, 3H), 8.91 (d, J=6.06 Hz, 2H), 9.04 (s, 1H), 11.51 (br. s., 1H).

Provenance & Evidence