Diisopropylethylamine → HCID 52916969, compound

Participants

Reaction Steps

To a solution of 3-(1-{[1-(4-fluoro-phenyl)-1H-pyrazolo[3,4-c]pyridine-4-carbonyl]-amino}-cyclopropyl)-benzoic acid (0.200 g, 0.480 mmol), Gly-OMe.HCl (68.1 mg, 0.543 mmol) and N,N-diisopropylethylamine (426 μL, 2.40 mmol) in DMF (4.5 mL) is added TBTU (192 mg, 0.600 mmol). After 4 hours, the mixture is concentrated in vacuo. The residue is dissolved in ethyl acetate (100 mL) and washed with 2N sodium hydroxide (3×50 mL), saturated aqueous ammonium chloride (2×50 mL), saturated aqueous sodium bicarbonate (50 mL), brine (50 mL). The organic layer is dried over MgSO4, filtered and concentrated. The residue is purified by silica gel chromatography eluting with a gradient of 0-8% methanol in methylene chloride to give a foam, which is triturated with ether (3 mL), filtered, washed with cold ether (3×3 mL) and air dried to afford the title compound.

Provenance & Evidence