Diisopropylethylamine → HCID 68380401, compound

Participants

Reaction Steps

5-(2-Methyl-1,3-oxazol-5-yl)-6-oxo-1,6-dihydropyridine-2-carboxylic acid (C39) (45 mg, 0.20 mmol) and 2-({2-[(7-fluoronaphthalen-1-yl)oxy]ethyl}amino)ethanol (C41) (55.8 mg, 1.1 mmol) were combined with dichloromethane (4 mL) and N,N-diisopropylethylamine (178 μL, 1.02 mmol). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 97%, 171 mg, 0.45 mmol) was added, and the reaction was stirred at room temperature for 18 hours. Saturated aqueous sodium bicarbonate solution was added and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 50% to 100% ethyl acetate in heptane, followed by elution with 20% methanol in ethyl acetate) was followed by high-pressure liquid chromatographic purification (Silica column, 5 μm; Gradient: 5% to 100% ethanol in heptane), to afford the title compound as a solid. Yield: 10 mg, 0.022 mmol, 11%. LCMS m/z 434.5 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.64 (s, 3H), 3.97-4.02 (m, 2H), 4.12-4.16 (m, 2H), 4.39-4.47 (m, 4H), 6.85 (d, J=7.6 Hz, 1H), 7.26-7.31 (m, 1H, assumed; partially obscured by solvent peak), 7.31-7.36 (m, 2H), 7.46 (d, J=8.2 Hz, 1H), 7.71 (dd, J=10.3, 2.5 Hz, 1H), 7.81 (dd, J=9.0, 5.5 Hz, 1H), 7.89 (d, J=7.6 Hz, 1H), 8.00 (s, 1H).

Provenance & Evidence