Potassium Carbonate → 1-[2-(4-{2-[2-(3,5-dimethoxyphenyl)ethyl]-5H-pyrrolo[2,3-b]pyrazin-6-yl}-1H-pyrazol-1-yl)ethyl]piperidin-4-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-piperidineethanol (7.9 mg, 0.0613 mmol) and triphenylphosphine (16.1 mg, 0.0613 mmol) in tetrahydrofuran (1.0 mL), diethyl azodicarboxylate (9.65 μL, 0.0613 mmol) was added at ambient temperature. After 15 minutes, a solution of 2-[2-(3,5-dimethoxyphenyl)ethyl]-5-(phenylsulfonyl)-6-(1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine (from Example 35, Step 1, 25 mg, 0.0510 mmol) in tetrahydrofuran (0.5 mL) was added. After 16 hours, the reaction was quenched with saturated aqueous NaHCO3, extracted with methylene chloride. The combined organic layers were dried over MgSO4, and then concentrated. The residue was dissolved in methanol (2 mL) and potassium carbonate (14.1 mg, 0.102 mmol) was added. The reaction mixture was then warmed up to 60° C. After 30 minutes, the crude mixture was cooled to ambient temperature and purified on RP-HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.05% TFA, at flow rate of 30 mL/min) to give the desired product (3.2 mg) as its TFA salt. LCMS calculated for C26H33N6O3 (M+H)+: m/z=477.3. Found: 477.2.

Provenance & Evidence