Diisopropylethylamine → HCID 178493008, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-1-[6-fluoro-1-(cis-3-methoxycyclobutyl)-1H-benzoimidazol-2-yl]ethylamine (160 mg, 0.61 mmol) in IPA (1.5 mL) was added 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (150 mg, 0.61 mmol) and DIPEA (0.53 mL, 3.1 mmol) and the reaction mixture heated at 90° C. for 16 h. After cooling to RT, the volatiles were removed under reduced pressure and the resulting residue loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined, concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-5% MeOH in DCM) to afford 396 as a white solid (120 mg, 52%). 1H NMR 6 (DMSO-d6): 8.24 (1H, s), 8.14 (1H, s), 7.90 (1H, d, J=7.84 Hz), 7.63 (1H, dd, J=8.82, 5.11 Hz), 7.54 (1H, dd, J=9.80, 2.47 Hz), 7.11-7.02 (1H, m), 5.84 (1H, s), 4.99-4.89 (1H, m), 3.81-3.72 (1H, m), 3.23 (3H, s), 2.96-2.59 (4H, m), 1.64 (3H, d, J=6.70 Hz)

Provenance & Evidence