Pyridine → HCID 90396913, compound

Participants

Reaction Steps

To a stirred solution of 2-(1-aminocyclopropyl)-5-phenyl-N-(pyridin-2-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (60.0 mg, 0.168 mmol) in DCM (10 mL) was added pyridine (0.0270 mL, 0.337 mmol) followed by methyl chloroformate (0.0140 mL, 0.185 mmol) and the reaction mixture stirred at RT for 2 h then concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 mL) and washed water (2×30 mL). The organic layer was separated, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC (Condition B-93 as described in general methods) to give methyl (1-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)cyclopropyl)carbamate (21.0 mg, 30.1%) as white solid. LCMS Condition B-34: retention time 2.29 min, [M+1]=415.0. HPLC Condition B-31: retention time 7.09 min, Purity 99.15%. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99-1.06 (m, 2H), 1.34-1.41 (m, 2H), 3.54 (s, 3H), 4.67 (d, J=4.8 Hz, 2H), 6.68 (d, J=2.7 Hz, 1H), 7.00 (s, 1H), 7.27 (ddd, J=7.5 Hz, J=4.9 Hz, J=1.1 Hz, 1H), 7.35 (d, J=7.9 Hz, 1H), 7.39-7.45 (m, 1H), 7.48-7.57 (m, 4H), 7.70 (d, J=2.7 Hz, 1H), 7.73-7.80 (m, 2H), 8.36-8.41 (m, 1H).

Provenance & Evidence