Ethylenediamine → HCID 58180971, compound

Participants

Reaction Steps

2,4-Difluorobenzoyl chloride (110 mg, 0.621 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; 0.26 g, 0.52 mmol), and triethylamine (216 μL, 0.00155 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, 0.05 mol) 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). The reaction mixture was stirred at RT for 30 min, and 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 C25H24F2N7O(M+H)+: m/z=476.2; Found: 476.0. 1H NMR (400 MHz, CD3OD): δ 8.96 (1H, d, J=10.0 Hz), 8.87 (1H, s), 8.51 (1H, s), 7.84 (1H, m), 7.38 (1H, m), 7.26 (1H, m), 7.06 (2H, m), 4.96 (1H, m), 4.59 (1H, m), 3.49 (2H, m), 3.15 (2H, m), 2.74 (1H, m), 2.23 (2H, m), 2.03 (1H, m), 1.86 (2H, m), 1.39 (1H, m), 1.28 (1H, m) ppm.

Provenance & Evidence