Diisopropylethylamine → [(S)-1-(6-Fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)-ethyl]-imidazo[2,1-f][1,2,4]triazin-4-yl-amine

Participants

Reaction Steps

(S)-1-(6-Fluoro-1-pyrid-2-yl-1H-benzoimidazol-2-yl)ethylamine (0.066 g, 0.26 mmol), 4-chloroimidazo[2,1-f][1,2,4]triazine (WO2010/014930) (0.040 g, 0.26 mmol) and diisopropylethylamine (0.090 mL, 0.52 mmol) in isopropanol (2 mL) was heated to 60° C. in a sealed tube for 0.5 h. The reaction mixture was cooled and diluted with EtOAc (20 mL) and washed with water (2 mL) The organic extracts were dried (Na2SO4), evaporated to dryness and purified by column chromatography (Si—PCC, gradient 0-10% (9:1 MeOH/0.880 NH3) in DCM). Product containing fractions were evaporated and freeze dried to give 322 as a white solid, (62 mg, 63%). LCMS (Method C): RT 3.78 min [M+H]+ 375.04. 1H NMR δ (ppm) (DMSO-d): 9.13 (1H, d, J=7.61 Hz), 8.57 (1H, dd, J=4.90, 1.81 Hz), 8.01-7.98 (2H, m), 7.93 (1H, s), 7.74-7.73 (2H, m), 7.55 (1H, d, J=1.12 Hz), 7.44-7.44 (1H, m), 7.15-7.15 (2H, m), 5.92 (1H, dq, J=7.11 Hz), 1.65 (3H, d, J=6.87 Hz)

Provenance & Evidence