Pyridine → HCID 78323677, 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 (80.0 mg, 0.201 mmol) was dissolved in CH2Cl2 (10 mL) and pyridine (0.0500 mL, 0.610 mmol) was added, followed by methanesulfonyl chloride (26.0 mg, 0.221 mmol). The reaction mixture was stirred at room temperature for 3 h then diluted with water (10 mL) and the aqueous solution was extracted with CH2Cl2 (25×2 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC (Condition B-64 as described in general methods) to obtain N-(5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridin-3-yl)methanesulfonamide (20.0 mg, 20.0%). LCMS Condition B-39: retention time 2.02 min, [M+1]=471.80. HPLC Condition B-32: retention time 6.96 min, Purity 99.40%. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.11 (s, 3H), 4.92 (d, J=4.8 Hz, 2H), 6.82 (d, J=2.8 Hz, 1H), 7.31 (dd, J=4.4 Hz, J=8.8 Hz, 2H), 7.46-7.61 (m, 8H), 7.79 (dt, J=2.0 Hz, J=7.6 Hz, 1H), 7.92 (d, J=2.8 Hz, 1H), 8.40 (d, J=4.0 Hz, 1H), 8.44 (t, J=2.4 Hz, 1H), 9.15 (d, J=2.0 Hz, 1H).

Provenance & Evidence