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

Participants

Reaction Steps

The title compound was prepared in the same manner as described in example 15 from 6-cyclopropyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (147 mg, 0.60 mmol), 3-(aminomethyl)-4-cyclohexyl-6-methyl-2(1H)-pyridinone trifluoroacetate (221 mg, 0.660 mmol), EDC (150 mg, 0.780 mmol), HOAT (106 mg, 0.780 mmol), N-methylmorpholine (0.264 mL, 2.400 mmol) and DMF (3 mL), wherein the stir time was 3 d and the final product was not treated with EtOH. The final product was collected as 193 mg (68%). LCMS E-S (M+H)=448.4. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.01-1.11 (m, 4H), 1.15-1.43 (m, 5H), 1.47 (d, J=6.57 Hz, 6H), 1.55-1.76 (m, 5H), 2.15 (s, 3H), 2.19-2.28 (m, 1H), 2.83 (t, J=11.12 Hz, 1H), 4.45 (d, J=5.05 Hz, 2H), 5.12 (spt, J=6.69 Hz, 1H), 6.02 (s, 1H), 7.37 (s, 1H), 8.21 (s, 1H), 8.74 (t, J=4.80 Hz, 1H), 11.56 (s, 1H).

Provenance & Evidence