Diisopropylethylamine → HCID 178461931, compound

Participants

Reaction Conditions

Reaction Steps

(S)-1-[6-Fluoro-1-(3-fluorophenyl)-1H-benzoimidazol-2-yl]ethylamine (0.45 g, 1.64 mmol) was dissolved in n-butanol (10 mL) and 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (0.39 g, 1.64 mmol) and DIPEA (1.45 mL, 8.24 mmol) were added. The reaction mixture was heated at 90° C. overnight. The resultant mixture was allowed to cool to RT and was concentrated in vacuo. The residue was passed down an Isolute® SCX-2 cartridge, eluting with DCM, MeOH and 2M NH3 in MeOH to afford crude product. This material was purified by column chromatography (silica gel, gradient 0-7.5% MeOH in DCM) to afford 185 as an off-white solid (100 mg, 20%). LCMS (Method K): RT 3.52 min [M+H]+ 392.0 1H NMR (DMSO-d6, 400 MHz): δ 8.09 (1H, s), 8.05 (1H, s), 7.91 (1H, s), 7.68 (1H, dd, J=8.80, 4.85 Hz), 7.58-7.47 (2H, m), 7.42 (1H, d, J=7.91 Hz), 7.32-7.23 (1H, m), 7.09 (1H, td, J=9.32, 2.48 Hz), 6.92 (1H, dd, J=8.93, 2.50 Hz), 5.63-5.47 (1H, m), 1.58 (3H, d, J=6.82 Hz)

Provenance & Evidence