2-Pyridinemethanamine → HCID 77843981, compound

Participants

Reaction Steps

5-(4-Hydroxy-5-phenylpyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (0.150 g, 0.408 mmol) was dissolved in THF (10 mL) and BOP reagent (0.271 g, 0.612 mmol) and DIPEA (0.214 mL, 1.23 mmol) were added. The reaction mixture was stirred at room temperature for 30 min. Pyridin-2-ylmethanamine (0.0660 g, 0.612 mmol) in THF (3 mL) was added to the reaction mixture and the resulting mixture was stirred at room temperature for 14 h. The reaction mixture was concentrated under reduced pressure and water was added to the residue. The aqueous layer was extracted with ethyl acetate (25×2 mL). The organic layer was dried (with anhydrous sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by CombiFlash (REDISEP®, silica gel, 40 g, 3% methanol in CH2Cl2) to afford 5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridine-3-sulfonamide (0.0400 g, 21.4%). LCMS Condition B-38: retention time 1.99 min, [M+1]=458.2. HPLC Condition B-32: retention time 7.75 min, Purity 98.90%. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.94 (d, J=4.4 Hz, 2H), 6.85 (d, J=2.8 Hz, 1H), 7.29 (dd, J=5.2 Hz, J=6.8 Hz, 1H), 7.42 (t, J=4.6 Hz, 1H), 7.46-7.50 (m, 2H), 7.52-7.56 (m, 2H), 7.60 (dd, J=2.0 Hz, J=6.8 Hz, 2H), 7.75 (s, 2H), 7.79 (dt, J=1.6 Hz, J=7.6 Hz, 1H), 7.96 (d, J=2.8 Hz, 1H), 8.39 (dd, J=0.8 Hz, J=1.6 Hz, 1H), 8.94 (t, J=2.0 Hz, 1H), 9.07 (d, J=2.4 Hz, 1H), 9.58 (d, J=2.0 Hz, 1H).

Provenance & Evidence