Diisopropylethylamine → HCID 178461908, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-[1-(tetrahydropyran-4-yl)-1H-benzoimidazol-2-yl]ethylamine from Example 17 (195 mg, 0.796 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (266 mg, 1.11 mmol) and DIPEA (0.25 mL, 1.43 mmol) in n-butanol (2 mL) was stirred in a sealed vial for 3 days at 120° C. After cooling to RT, volatiles were removed under reduced pressure and the resulting residue was loaded into an Isolute® SCX-2 which was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) and then triturated with a mixture EtOAc and MeOH affording 127 as an off-white solid (148 mg, 51%). LCMS: RT 2.29 min [M+H]+ 364.0. 1H NMR (DMSO, 400 MHz): δ 12.93 (1H, bs), 8.30-7.81 (3H, m), 7.61-7.59 (2H, m), 7.17-7.03 (2H, m), 5.96 (1H, bs), 4.81-4.63 (1H, m), 3.94 (1H, d, J=11.07 Hz), 3.74 (1H, d, J=11.25 Hz), 3.35 (1H, bs), 2.84 (1H, bs), 2.47-2.35 (1H, m), 2.30-2.17 (1H, m), 1.75 (1H, bd), 1.64 (3H, d, J=6.71 Hz), 1.50 (1H, bs)

Provenance & Evidence