Pyridine → HCID 90386153, 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 (15 mL) was added pyridine (0.0200 mL, 0.253 mmol) followed by methanesulfonylchloride (0.0200 mL, 0.253 mmol) and the reaction stirred at RT for 2 h then concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 mL) and washed with 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-94 as described in general methods) to give N-(1-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)cyclopropyl)methanesulfonamide (26.0 mg, 35.5%) as white solid. LCMS Condition B-34: retention time 2.32 min, [M+1]=435.0. HPLC Condition B-31: retention time 7.72 min, Purity 99.61%. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.25-1.31 (m, 2H), 1.36-1.42 (m, 2H), 2.99 (s, 3H), 4.71 (d, J=4.8 Hz, 2H), 6.71 (d, J=2.7 Hz, 1H), 7.07 (t, J=4.8 Hz, 1H), 7.27 (ddd, J=6.8 Hz, J=5.5 Hz, J=1.0 Hz, 1H), 7.36 (d, J=7.8 Hz, 1H), 7.41-7.45 (m, 1H), 7.47-7.57 (m, 4H), 7.72-7.77 (m, 2H), 8.06 (s, 1H), 8.35-8.40 (m, 1H).

Provenance & Evidence