Diisopropylethylamine → HCID 178517966, compound

Participants

Reaction Steps

To a solution of 3.0 g (7.188 mmol) 4-(cyclohexylamino)-1-(3-fluorophenyl)-2-oxo-1,3-diaza-8-azoniaspiro[4.5]dec-3-ene dihydrochloride in 30 mL THF:AcOH (9:1) was added 1.8 g (12.005 mmol) 3-formylphenylboronic acid and 5.53 g (21.567 mmol) PS-DIEA resin and 5.97 g (14.388 mmol) MP-cyanoborohydride resin. The heterogeneous reaction mixture was stirred at rt for 24 hrs, then filtered, washed with 100 mL methanol, and concentrated. Purification by automated flash chromatography (8-30% CH3CN/H2O over 41 min, 0.05% added TFA reverse phase YMC ODSA 120 Å, 15-30 μM particle size,) afforded 3-{[4-(cyclohexylamino)-1-(3-fluorophenyl)-2-oxo-1,3,8-triazaspiro[4.5]dec-3-en-8-yl]methyl}phenylboronic acid as a solid. 1H NMR (CD3OD, 400 MHz) δ 7.44 (m, 1H), 7.38 (d, J=7.32 Hz, 1H), 7.29 (s, 1H), 7.18 (m, 1H), 7.09 (m, 3H) 6.93 (m, 1H), 3.75 (m, 1H), 3.31 (s, 2H), 2.78 (m, 2H), 2.12 (m, 4H), 1.97 (m, 4H), 1.78 (m, 2H), 1.65 (m, 1H), 1.35 (m, 5H). High resolution mass spec (FT/ICR) calc M+H=478.2661 found 478.2709.

Provenance & Evidence