Diisopropylethylamine → HCID 178461937, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-[6-fluoro-1-(2-methyl-2H-pyrazol-3-yl)-1H-benzoimidazol-2-yl]-ethylamine, (0.093 g, 0.36 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (0.119 g, 0.50 mmol) and DIPEA (0.12 mL, 0.65 mmol) in IPA (2 mL) was stirred at 80° C. in a sealed tube for 16 h. After cooling, the reaction mixture was concentrated in vacuo and the residue purified by chromatography (SiO2, 0-8% (2M ammonia in methanol) in DCM). The product was dissolved in methanol (4 mL) and treated with HCl/dioxane (4M, 0.6 mL, 2.4 mmol) then stirred for 30 minutes. The resulting mixture was concentrated in vacuo and residue loaded onto an Isolute® SCX-2 cartridge and washed with MeOH. The product was eluted with 2M NH3/MeOH then concentrated in vacuo to give 417 as a white solid (0.078 g, 58%). LCMS (Method K): RT 2.79, 2.95 min [M+H]+ 378.0. 1H NMR (DMSO-d6, 400 MHz): δ 12.91-12.00 (1H, m), 8.30-7.81 (3H, m), 7.78-7.71 (1H, m), 7.50 (1H, s), 7.23-7.03 (1H, m), 7.03-6.92 (1H, m), 6.69-6.51 (1H, m), 5.60-5.22 (1H, m), 3.62-3.55 (3H, m), 1.65-1.54 (3H, m). Signals split due to presence of rotamers/tautomers

Provenance & Evidence