N,N-Dimethylethylenediamine → HCID 56598279, 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-aminoethyl)dimethylamine (37.7 mg, 0.43 mmol) in NMP (2 mL). The vessel was sealed and the reaction mixture was irradiated (microwave) at 150° C. for 1 h. The mixture was evaporated under vacuum, and the resulting residue was partitioned between EtOAc and water. The contents were extracted with EtOAc, DCM and DCM/isopropanol (70:30). The combined organics were washed with water (2×) and brine, dried over MgSO4, filtered and evaporated. 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 and sonicated. Solids that precipitated were filtered, washed with hexanes, and dried to afford the title compound (60 mg, 65%) as a white solid. LCMS E-S (M+H)=425.9. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.55 (br. s., 1 H) 8.43 (t, J=5.05 Hz, 1 H) 7.84 (s, 1 H) 7.08 (t, J=5.05 Hz, 1 H) 6.67 (s, 1 H) 5.89 (s, 1 H) 4.94 (quin, J=6.63 Hz, 1 H) 4.32 (d, J=5.05 Hz, 2 H) 3.44 (q, J=6.48 Hz, 2 H) 2.44 (t, J=6.69 Hz, 2 H) 2.17-2.22 (m, 9 H) 2.12 (s, 3 H) 1.43 (d, J=6.57 Hz, 6 H).

Provenance & Evidence