Diisopropylethylamine → HCID 178463563, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(6-fluoro-1-pyridin-4-yl-1H-benzoimidazol-2-yl)ethylamine (60 mg, 0.23 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (59 mg, 0.25 mmol) and DIPEA (125 μL, 0.70 mmol) in n-butanol (0.5 mL) was heated at 100° C. in a sealed vial for 23 h. After cooling to RT, the resulting mixture was diluted with MeOH and loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined, concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) followed by reverse phase HPLC (Phenomenex Gemini 5 μm C18 on a gradient 5-60%, 0.1% NH4OH in acetonitrile/water) to afford 303 as a pale orange solid (12 mg, 14%). LCMS (Method K): RT 2.70 min [M+H]+ 375.05. 1H NMR (DMSO-d6, 400 MHz): δ 12.90 (1H, s), 8.72-8.66 (2H, m), 8.09-8.01 (2H, m), 7.73-7.67 (3H, m), 7.19-7.01 (2H, m), 5.68-5.11 (1H, m), 1.62 (3H, d, J=7.26 Hz)

Provenance & Evidence