Pyridine → HCID 90386083, compound

Participants

Reaction Steps

2-(5-Aminopyridin-3-yl)-5-phenyl-N-(pyridin-2-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (0.200 g, 0.508 mmol) was dissolved in DCM (5 mL) and pyridine (0.0820 mL, 1.02 mmol) was added, followed by the addition of methyl 2-chloro-2-oxoacetate (0.0620 g, 0.508 mmol). The reaction mixture was stirred at room temperature for 30 min. The reaction mixture was quenched by the addition of water (10 mL) and the mixture extracted with CH2Cl2 (4×10 mL). The combined organic layer was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford methyl 2-oxo-2-((5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridin-3-yl)amino)acetate (0.180 g, 70.2%). The residue was taken for the next step without further purification. LCMS Condition B-80: retention time 2.32 min, [M+1]=480.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.90 (s, 3H), 4.93 (d, J=4.7 Hz, 2H), 6.83 (d, J=2.8 Hz, 1H), 7.25-7.39 (m, 2H), 7.44-7.63 (m, 6H), 7.79 (td, J=7.7 Hz, J=1.8 Hz, 1H), 7.92 (d, J=2.8 Hz, 1H), 8.36-8.41 (m, 1H), 8.95-9.05 (m, 2H), 9.19 (d, J=1.8 Hz, 1H), 11.20 (s, 1H).

Provenance & Evidence