HCID 90431675, compound → HCID 90386199, compound

Participants

Reaction Steps

To a stirred solution of (E)-tert-butyl (2-(5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridin-3-yl)vinyl)sulfonylcarbamate (100 mg, 0.171 mmol) in EtOAc (20 mL) was added 10% Pd/C (36.5 mg, 0.343 mmol) and the reaction mixture stirred for 12 h at RT under the H2 atmosphere using a bladder. The reaction mixture was filtered through a pad of CELITE® and the filtrate was treated with TFA (1 mL) then stirred at RT for 4 h. The volatile components were removed under reduced pressure. The resulting residue was dissolved in DCM (100 mL) and washed with 10% NaHCO3 (50 mL). The organic layer was separated, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC (Condition B-95 as described in general methods) to give 2-(5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)pyridin-3-yl)ethanesulfonamide (15.0 mg, 18.0%). LCMS Condition B-83: retention time 0.995 min, [M+1]=486.0, Purity: 96.17%. 1H NMR (400 MHz, CD3OD) δ ppm 3.24-3.30 (m, 2H), 3.42-3.52 (m, 2H), 4.90-4.93 (m, 2H), 6.77 (d, J=2.7 Hz, 1H), 7.30 (dd, J=7.0 Hz, J=5.3 Hz, 1H), 7.43-7.48 (m, 2H), 7.49-7.56 (m, 2H), 7.58-7.63 (m, 2H), 7.76 (d, J=2.7 Hz, 1H), 7.80 (td, J=7.7 Hz, J=1.8 Hz, 1H), 8.46 (d, J=4.2 Hz, 1H), 8.50-8.56 (m, 2H), 9.25 (d, J=2.0 Hz, 1H).

Provenance & Evidence