Ethanolamine → HCID 56598280, compound

Participants

Reaction Steps

In a 25 mL sealable tube under nitrogen were combined 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-aminoethanol (1 ml) in NMP (2 mL). The vessel was sealed and the reaction mixture was irradiated (microwave) at 130° C. for 1 h and then at 140° C. for 90 min. The mixture was evaporated under vacuum and the residue was purified by silica gel chromatography (eluent: gradient 0 to 90:10:1 DCM/MeOH/NH4OH). The isolated yellow oil was treated with EtOAc, sonicated, and treated with hexanes. The solids were filtered, dissolved in DMF (1 mL), and a few drops of water were added. The solution was allowed to stand at room temperature overnight, and then sonicated. The filtered solid was washed with Hexanes/EtOAc (1:1), and then dried to afford the title compound (55 mg, 63%) as a light yellow solid. LCMS E-S (M+H)=399.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.56 (br. s., 1H) 8.44 (br. s., 1H) 7.84 (s, 1H) 7.20 (br. s., 1H) 6.68 (s, 1H) 5.89 (s, 1H) 4.95 (dt, J=13.01, 6.38 Hz, 1H) 4.72 (t, J=4.93 Hz, 1H) 4.32 (d, J=4.80 Hz, 2H) 3.58 (d, J=5.56 Hz, 2H) 3.38-3.46 (m, 2H) 2.21 (s, 3H) 2.12 (s, 3H) 1.43 (d, J=6.57 Hz, 6H)

Provenance & Evidence