1-Cyclopentyl-3-methyl-1H-pyrazol-5-amine → ethyl 1-cyclopentyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

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Reaction Steps

The title compound was prepared in the same manner as described for intermediate 33 using 1-cyclopentyl-3-methyl-1H-pyrazol-5-amine (570 mg, 3.45 mmol), ethyl 4-cyclopropyl-2,4-dioxobutanoate (635 mg, 3.45 mmol), and benzene (50 mL) wherein the reaction time was 4 h. The crude product was purified via silica gel chromatography (eluent: 0 to 10% EtOAc:Hex). The final product was collected as 0.740 g (68%). LCMS E-S (M+H)=314.3 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.04-1.21 (m, 4H) 1.47 (t, J=7.20 Hz, 3H) 1.73 (br. s., 2H) 2.00 (d, J=2.78 Hz, 2H) 2.08-2.16 (m, 4H) 2.21 (s, 1H) 2.67 (s, 3H) 4.49 (q, J=7.16 Hz, 2H) 5.32 (t, J=7.83 Hz, 1H) 7.40 (s, 1H).

Provenance & Evidence