Ethylenediamine → HCID 58180899, compound

Participants

Reaction Steps

1-Methyl-1H-pyrazole-3-sulfonyl chloride (108 mg, 0.597 mmol), 4-piperidin-4-yl-3-[4-(7-{[2-(trimethylsilypethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile hydrochloride (from example 5, step 4; 250 mg, 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 (4 mL) and trifluoroacetic acid (4 mL, 0.05 mol) for 30 min, evaporated under reduced pressure. To the resultant residue was added methanol (5 mL) and ethylenediamine (0.5 mL, 0.007 mol). The resulting 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 (183 mg, 76.6%). LCMS calculated for C22H26N9O2S(M+H)+: m/z=480.2; Found: 480.0. 1H NMR (300 MHz, CD3OD): δ 8.92 (1H, s), 8.86 (1H, s), 8.49 (1H, s), 7.83 (1H, d, J=3.6 Hz), 7.69 (1H, d, J=2.1 Hz), 7.23 (1H, d, J=3.6 Hz), 6.59 (1H, d, J=2.1 Hz), 4.94 (1H, m), 3.89 (3H, s), 3.70 (2H, m), 3.12 (2H, m), 2.33 (2H, m), 2.19 (1H, m), 1.94 (1H, m), 1.82 (1H, m), 1.58 (1H, m), 1.32 (2H, m), 1.05 (1H, m) ppm.

Provenance & Evidence