Diisopropylethylamine → HCID 178456070, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-((S)-1-amino-propyl)-5-fluoro-3-phenyl-3H-benzoimidazole-4-carbonitrile (0.260 g, 0.88 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (0.290 g, 1.24 mmol) and DIPEA (0.28 mL, 1.59 m mol) in IPA (2 mL) was stirred at 90° C. in a sealed tube for 16 h. The resulting mixture was concentrated in vacuo and the residue purified by chromatography (SiO2 0-10% (2M ammonia in methanol) in DCM). The product was dissolved in methanol and treated with HCl/dioxane (4M, 1.1 mL, 0.00450 mol) and stirred for 20 minutes. The mixture was loaded onto an Isolute® SCX-2 cartridge, washed with MeOH and the product eluted with 2M NH3/MeOH then concentrated in vacuo. The resulting residue was purified by chromatography (SiO2, 0-10% (2M ammonia in methanol) in DCM) to give 244 as a white solid (0.205 g, 57%). LCMS (method K): Rt 3.51 min, [M+H]+ 413. 1H NMR (DMSO-d6): δ 13.20-12.50 (1H, bs), 9.60 (1H, s), 8.00 (1H, s), 7.71 (1H, m), 7.60 (2H, s), 7.51-7.49 (3H, m), 7.11-7.08 (1H, m), 6.86 (1H, m), 5.64 (1H, m), 2.10 (3H, s), 1.50 (3H, d, J=6.81 Hz)

Provenance & Evidence