Diisopropylethylamine → HCID 178448884, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-1-(6-fluoro-1-pyridin-3-yl-1H-benzoimidazol-2-yl)-2-methylpropylamine (135 mg, 0.48 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (110 mg, 0.48 mmol) and DIPEA (0.4 mL, 2.4 mmol) in n-butanol (2 mL) was heated for 18 h at 100° C. in a sealed vial. 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 was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) to afford 206 (75 mg, 39%). LCMS (Method K): RT 3.19 min [M+H]+ 403.0. 1H NMR (DMSO-d6, 400 MHz): δ 12.85 (1H, s), 8.86-8.59 (2H, m), 8.18-7.88 (3H, m), 7.79-7.47 (3H, m), 7.11 (1H, td, J=9.31, 2.48 Hz), 6.93 (1H, br d, J=8.83 Hz), 5.21 (1H, br s), 0.99-0.90 (4H, m), 0.85 (3H, br s)

Provenance & Evidence