Ethylenediamine → HCID 58180949, compound

Participants

Reaction Steps

4-Fluoro benzoyl chloride (94.7 mg, 0.597 mmol), 4-piperidin-4-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile hydrochloride (from example 5, step 4; 0.250 g, 0.498 mmol), and triethylamine (208 μL, 0.00149 mol) were dissolved in acetonitrile (2.5 mL). The mixture was stirred at RT for 1 h. Solvents were evaporated. The crude product was treated with DCM (3 mL) and trifluoroacetic acid (3 mL, 0.04 mol) for 30 min, and evaporated to dryness under reduced pressure. To the resultant residue was added methanol (5 mL) and ethylenediamine (0.5 mL, 0.007 mol) and the resulting mixture was stirred at RT for 30 min. After being concentrated 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 60 mL/min) to give the desired product. LCMS calculated for C25H25FN7O(M+H)+: m/z=458.2; Found: 458.0. NMR (300 MHz, CD3OD) δ 9.01 (1H, s), 8.90 (1H, s), 8.54 (1H, s), 7.89 (1H, d, J=3.6 Hz), 7.42 (2H, m), 7.31 (1H, d, J=3.6 Hz), 7.17 (2H, m), 4.98 (1H, m), 4.55 (1H, m), 3.52 (2H, m), 3.16 (2H, m), 2.73 (1H, m), 2.25 (2H, m), 2.03 (1H, m), 1.88 (2H, m), 1.38 (1H, m), 1.28 (1H, m) ppm.

Provenance & Evidence