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

Participants

Reaction Steps

A DMF solution (6 mL) of 1-(1-methylethyl)-6-(4-pyridinyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (288 mg, 1.019 mmol), 3-(aminomethyl)-6-methyl-4-(1-methylethyl)-2(1H)-pyridinone.TFA (300 mg, 1.019 mmol), HOAT (208 mg, 1.529 mmol), EDC (782 mg, 4.08 mmol), and N-methylmorpholine (0.448 mL, 4.08 mmol) was stirred overnight at 40° C. After cooling to room temperature, the reaction mixture was poured into H2O (50 mL) and EtOAc (50 mL). The aqueous layer was extracted with EtOAC (2×50 mL). The organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in DMSO and purified by reverse phase (15-40% ACN in H2O, 0.1% TFA). The product fractions were poured into sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound as a white solid (123 mg, 27% yield). LCMS E-S (M+H)=445.4. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (m, 6 H), 1.56 (m, 6 H), 2.17 (s, 3 H), 3.17-3.28 (m, 1 H), 4.45-4.56 (m, 2 H), 5.29-5.43 (m, 1 H), 5.99-6.12 (m, 1 H), 8.16-8.23 (m, 2 H), 8.24-8.29 (m, 1 H), 8.40-8.46 (m, 1 H), 8.71-8.82 (m, 2 H), 8.96-9.04 (m, 1 H), 11.53-11.63 (m, 1 H).

Provenance & Evidence