4-Piperidinamine → HCID 56598147, 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 (60 mg, 0.16 mmol) and 4-piperidinamine (2 mL) in EtOH (3 mL). The vessel was sealed and the reaction mixture was irradiated (microwave) at 125° C. for 5 hr and then at 160° C. for 90 min. The mixture was evaporated under vacuum and the resulting residue was partitioned between EtOAc and water. 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 product was treated with EtOAc/ether (1:1) and allowed to stand at room temperature overnight. The solids that had precipitated were triturated, filtered, and dried to afford the title compound as a pale yellow solid 25 mg (35%). LCMS E-S (M+H)=438.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.66 (t, J=4.67 Hz, 1 H) 7.98 (s, 1 H) 7.12 (s, 1 H) 5.89 (s, 1 H) 4.98 (dt, J=13.33, 6.60 Hz, 1 H) 4.30-4.41 (m, 4 H) 3.01 (t, J=11.62 Hz, 2 H) 2.85 (br. s., 1 H) 2.20 (s, 3 H) 2.12 (s, 3 H) 1.80 (d, J=10.36 Hz, 2 H) 1.44 (s, 3 H) 1.43 (s, 3 H) 1.18-1.30 (m, 3 H) 0.79-0.91 (m, 1 H)

Provenance & Evidence