Ethylamine → N-[(4,6-Dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-(ethylamino)-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Participants

Reaction Steps

To a 10 mL microwave vial equipped with stir bar, septum cap and nitrogen inlet were added 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (23 mg, 0.062 mmol) and ethanol (1 mL). Added next to the stirring suspension was ethylamine (0.100 mL, 1.230 mmol) via syringe at once. The sealed reaction mixture was irradiated (microwave) at 110° C. for 40 min, followed by addition of 0.1 mL ethylamine and further irradiation for 7 hr at 130° C. After cooling to room temperature, about 50% of the volatiles were removed by a stream of nitrogen. The reaction mixture was diluted with water (20 mL) and stirred for 10 min. The mixture was then filtered and the collected solid washed with water. The solid was dried in vacuum oven at 50° C. for 18 h, to afford the title compound as 0.17 g (71%). LCMS E-S (M+H)=383.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.17 (t, J=7.07 Hz, 3 H), 1.43 (d, J=6.57 Hz, 6 H), 2.12 (s, 3 H), 2.21 (s, 3 H), 3.35-3.39 (m, 2 H), 4.31 (d, J=5.05 Hz, 2 H), 4.89-5.01 (m, 1 H), 5.89 (s, 1 H), 6.61 (s, 1 H), 7.18 (t, J=5.31 Hz, 1 H), 7.83 (s, 1 H), 8.44 (t, J=5.05 Hz, 1 H), 11.55 (br. s., 1 H).

Provenance & Evidence