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

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Reaction Steps

The title compound was prepared in the same manner as described in example 19 from 6-cyclopropyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.12 g, 0.489 mmol), 1-hydroxy-7-azabenzotriazole (0.100 g, 0.734 mmol), 3-(aminomethyl)-6-methyl-4-(trifluoromethyl)-2(1H)-pyridinone (0.154 g, 0.636 mmol, DMSO (3.0 mL), N-methylmorpholine (0.215 mL, 1.957 mmol), and EDC (0.141 g, 0.734 mmol) The crude solid was purified by silica gel chromatography (eluent: gradient 5-100% of 10% 2M NH3 (in MeOH/DCM) and DCM) and the collected product dried in vacuum oven for 5 h. The final product was collected as 0.112 g (50%). LCMS E-S (M+H)=434.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.03-1.12 (m, 4 H), 1.47 (d, J=6.82 Hz, 6 H), 2.20-2.33 (m, 4 H), 4.34-4.54 (m, 2 H), 5.12 (quin, J=6.63 Hz, 1 H), 6.33 (s, 1 H), 7.39 (s, 1 H), 8.18 (s, 1 H), 8.70 (t, J=4.04 Hz, 1 H), 12.43 (s, 1 H).

Provenance & Evidence