Diisopropylethylamine → HCID 178463558, compound

Participants

Reaction Conditions

Reaction Steps

(S)-1-[6-Fluoro-1-(2-fluorophenyl)-1H-benzoimidazol-2-yl]ethylamine (0.22 g, 0.81 mmol) was dissolved in n-butanol (5 mL) and 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (0.193 g, 0.81 mmol) and DIPEA (0.70 mL, 4.03 mmol) added. The reaction mixture was heated at 100° C. overnight. The resultant mixture was allowed to cool to RT and then concentrated in vacuo. The residue was passed down an Isolute® SCX-2 cartridge, eluting with DCM, MeOH and 2M NH3 in MeOH to afford a light yellow gum. This was purified by column chromatography (silica gel, gradient 0-5% MeOH in DCM) to afford 195 as an off-white solid (209 mg, 67%). LCMS (Method K): RT 3.34/3.52 min [M+H]+ 392.0 1H NMR (DMSO-d6, 400 MHz): δ 8.16-7.79 (3H, m), 7.77-7.64 (2H, m), 7.58-7.21 (3H, m), 7.16-7.09 (1H, m), 6.92-6.83 (1H, m), 5.63-5.38 (1H, m), 1.69 (1.5H, d, J=6.85 Hz), 1.58 (1.5H, d, J=6.86 Hz). NMR signals represent a mixture of rotamers

Provenance & Evidence