Triphenylphosphine → 5-Nitro-8-(2-{[3-(1-piperazinyl)-2-pyrazinyl]oxy}ethoxy)quinoline, Hydrochloride

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Reaction Steps

DEAD (0.485 mL, 3.08 mmol) was added to a stirred solution of 2-[3-(4-tert-butoxycarbonyl-1piperazinyl)-2-pyrazinyloxy]ethanol (1.00 g, 3.08 mmol; prepared in Example 52, Step 2), 8-hydroxy-5-nitroquinoline (0.589 g, 3.08 mmol) and PPh3 (0.85 g, 3 24 mmol) in THF (10 mL). The mixture was stirred at room temperature for 2 h, and concentrated. The residue was passed through a silica column using toluene/EtOAc (1.1) as eluent The N-Boc protected intermediate obtained was treated with CH2Cl2/TFA/H2O (50:45:5, 15 mL) for 30 min at room temperature and concentrated. The residue was dissolved in 0 1 M aqueous HCl and washed with toluene The water phase was concentrated to give 0.206 g (15%) of the title product. Pos-EI-MS shows M= and 7 ions supporting the stated structure: HRMS m/z calcd for C19H20N6O4 (M)+396.1546, found 396.1557.

Provenance & Evidence