Ethylenediamine → 4-[(4-{3-cyano-2-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propyl}piperazin-1-yl)carbonyl]benzonitrile

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Reaction Steps

4-Cyanobenzoyl chloride (7.91 mg, 0.0478 mmol), 4-piperazin-1-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile hydrochloride (from example 1, step 4; 0.02 g, 0.0398 mol) and triethylamine (16.6 μL, 0.119 mmol) were dissolved in acetonitrile (0.2 mL). The mixture was stirred at RT for 1 h. Solvents were evaporated and the crude product was treated with DCM (0.2 mL) and trifluoroacetic acid (0.2 mL, 0.002 mol) for 30 min. The reaction mixture was concentrated under reduced pressure. To the residue was added methanol (1 mL) and ethylenediamine (0.1 mL, 0.001 mol) and the resultant mixture was stirred at RT for 30 min and evaporated under reduced pressure. The residue was purified on RP-HPLC (XBridge C-18 Column, eluting with a gradient of acetonitrile/water containing 0.15% NH4OH, at flow rate 30 mL/min) to give the desired product. LCMS calculated for C25H24N9O(M+H)+: m/z=466.2; Found 466.0.

Provenance & Evidence