Diisopropylethylamine → HCID 22347040, compound

Participants

Reaction Steps

A mixture of 2-{4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidino}acetic acid (0.06 g, 0.00013 mol), 2-aminoimidazole sulfate (0.022 g, 0.000163 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.031 g, 0.000163 mol), N,N-diisopropylethylamine (0.047 g, 0.00036 mol) and 1-hydroxy-7-azabenzotriazole (0.018 g, 0.00013 mol) in anhydrous dichloromethane (8 mL) was stirred for 18 hours at room temperature. Additional 2-aminoimidazole sulfate (0.022 g, 0.000163 mol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.031 g, 0.000163 mol), N,N-diisopropylethylamine (0.047 g, 0.00036 mol) and 1-hydroxy-7-azabenzotriazole (0.018 g, 0.00013 mol), were added and the mixture was stirred for 18 hour at room temperature. The mixture was warmed to 50° C. for 6 hours, then stirred at room temperature for 2 days. The solvent was removed under reduced pressure. The residue was purified by RP-HPLC (Hypersilprep HS C18, 8 μm, 250×21.1 mm; 5%-100% over 35 min with 0.1 M ammonium acetate, 21 mL/min) to yield N1-(1H-2-imidazolyl)-2-{4-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidino}acetamide (0.005 g, 0.00001 mol).

Provenance & Evidence