Diisopropylethylamine → HCID 178456862, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-(6-fluoro-1-pyridin-3-yl-1H-benzoimidazol-2-yl)propylamine (243 mg, 0.90 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (210 mg, 0.90 mmol) and DIPEA (780 μL, 4.5 mmol) in n-butanol (3 mL) was heated at 100° C. in a sealed vial for 18 h. After cooling to RT, the volatiles were removed under reduced pressure and the resulting residue loaded onto an Isolute® SCX-2 cartridge and washed with MeOH followed by 2M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) to afford 205 (145 mg, 42%). LCMS (Method K): RT 2.96 min [M+H]+ 389.1. 1H NMR (DMSO-d6, 400 MHz): δ 12.65 (1H, s), 8.81 (1H, d, J=2.47 Hz), 8.67 (1H, br s), 8.21-8.01 (3H, m), 7.91 (1H, br s), 7.73 (1H, dd, J=8.81, 4.84 Hz), 7.56 (1H, br s), 7.18-7.08 (1H, m), 6.95 (1H, dd, J=8.88, 2.48 Hz), 5.35 (1H, br s), 2.19-2.01 (2H, m), 0.90 (3H, t, J=7.32 Hz)

Provenance & Evidence