Potassium Carbonate → 3-(3,5-dichlorophenoxy)-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridine-3-yl}methyl)-4-(trifluoromethyl)pyridine-2(1H)-one

To 3-(3,5-dichlorophenoxy)-4-(trifluoromethyl)pyridine-2(1H)-one (0.400 g, 1.23 mmol) and potassium carbonate (0.171 g, 1.23 mmol) suspended in dimethylformamide (5 mL) was added 3-(chloromethyl)-N,1-bis(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine-6-amine (0.522 g, 1.23 mmol) as a solution in dimethylformamide (2 mL). The reaction mixture was allowed to stir at room temperature. After 16 hours, the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine (3×100 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to afford the title compound as a solid. 1H NMR (DMSO-d6) δ 7.90 (d, J=7.3 Hz, 1H), 7.75-7.67 (m, 1H), 7.52 (d, J=8.8 Hz, 1H), 7.34-7.30 (m, 1H), 7.27 (d, J=8.4 Hz, 2H), 7.13 (d, J=8.6 Hz, 2H), 7.07-7.03 (m, 2H), 6.83 (d, J=8.6 Hz, 2H), 6.77 (d, J=8.6 Hz, 2H), 6.59 (d, J=7.3 Hz, 1H), 6.40 (d, J=8.8 Hz, 1H), 5.31 (s, 2H), 5.29 (s, 2H), 4.48 (d, J=4.3 Hz, 2H), 3.71 (s, 3H), 3.69 (s, 3H). HRMS (M+1)=710.1557.

1. extractionextracted with ethyl acetate (2×100 mL)
2. washThe combined organic extracts were washed with brine (3×100 mL)
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. customthe solvent was evaporated under reduced pressure

ORD-Eintrag

ord-66718712a5cd49adb60cd150b5c4f377

Quelldatensatz

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08404856B2