N~1~-(Pyridin-2-yl)ethane-1,2-diamine → HCID 56598814, compound

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Reaction Steps

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 (80 mg, 0.21 mmol) and (2-aminoethyl)2-pyridinylamine (88 mg, 0.64 mmol) were suspended in 2 mL of NMP and irradiated (microwave) as follows: 180° C. for 30 min, 200° C. for 30 min, 220° C. for 30 min, 230° C. for 30 min and then 240° C. for 1 h. After cooling to room temperature, some of the solvent was removed in vacuo and the residue was purified by silica gel chromatography (eluent: DCM/MeOH/NH4OH, gradient 0 to 90:10:1). The collected solid was partitioned between water and EtOAc/toluene (1:1) and then extracted twice with DCM/isopropanol. The combined organic layers were washed with water, dried over MgSO4, filtered, and concentrated in vacuo to afford a dark brown oil. After drying under vacuum overnight, the residue was again purified by silica gel chromatography (eluent: DCM/MeOH/NH4OH (gradient 0 to 90:10:1). The collected solid was suspended in EtOH, sonicated, and filtered. The solid was further washed with EtOH/DCM, filtered, and dried in vacuum-oven for 2 days. The final product was collected as 47 mg (45%). LCMS E-S (M+H)=475.0 1H NMR (400 MHz, DMSO-d6) δ ppm 11.56 (br. s., 1 H) 8.47 (t, J=5.05 Hz, 1 H) 7.97 (dd, J=4.93, 1.14 Hz, 1 H) 7.85 (s, 1 H) 7.32-7.39 (m, 2 H) 6.65 (s, 1 H) 6.61 (t, J=5.43 Hz, 1 H) 6.46-6.51 (m, 2 H) 5.89 (s, 1 H) 4.97 (quin, J=6.69 Hz, 1 H) 4.32 (d, J=5.05 Hz, 2 H) 3.49 (dt, J=15.28, 5.62 Hz, 4 H) 2.21 (s, 3 H) 2.13 (s, 3 H) 1.44 (s, 3 H) 1.43 (s, 3 H).

Provenance & Evidence