Water → HCID 58529438, compound

Participants

Reaction Conditions

Reaction Steps

5-(2-benzyl-2H-indazol-6-yl)-7-(3-piperazin-1-yl-propyl)pyrrolo-[2,1-f][1,2,4]triazin-4-ylamine (75 mg, 0.16 mmol) was dissolved in anhydrous DMF (3.2 mL) and treated with EtN(iPr)2 (44 μL, 0.32 mmol) followed by the addition of propionyl chloride (22 μL, 0.24 mmol). The mixture was heated to 50° C. for 18 h, cooled to rt and poured into water. The aqueous layer was extracted with 3×10 mL of EtOAc and the combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude was purified via preparative HPLC. The product containing fractions were collected, and the TFA from the eluent was removed via filtration through an acidic resin followed by washing with acetonitrile. The product was then eluted with 2M NH3 in MeOH. The filtrate was concentrated and the residue was crystallized from DCM-ether to provide the title compound (35.5 mg, 42%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 8.54 (s, 1H), 7.88 (s, 1H), 7.79 (d, 1H), 7.57 (s, 1H), 7.36 to 7.28 (m, 5H), 7.13 (dd, 1H), 6.60 (s, 1H), 5.63 (s, 2H), 3.41-3.31 (m, 4H), 2.89 (t, 2H), 2.38 to 2.24 (m, 8H), 1.90 to 1.84 (m, 2H), 0.93 (t, 3H); ES-MS m/z 523.3 [M+H]+, RT (min) 2.15.

Provenance & Evidence