반응 #47284
ord-96ce387522614b439ff2904fafa62192
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후처리
- 1세척washed with saturated ammonium chloride, water
- 2건조a saturated sodium chloride solution and dried over sodium sulfate
- 3농축The organic layer was concentrated
- 4기타the crude product was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 12 g, 0% to 100% ethyl acetate/hexanes)
실험 절차
A solution of (S)-2-[4-(2-chloro-6-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-cyclohexyl-propionic acid (prepared as in Example 67, 125 mg, 0.33 mmol) in N,N-dimethylformamide (3 mL) was treated with 1-methyl-1H-pyrazol-3-ylamine (40 mg, 0.40 mmol), benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (300 mg, 0.67 mmol) and N,N-diisopropylethylamine (85 mg, 0.65 mmol). The reaction mixture was stirred for 4 h at 25° C., under nitrogen. The reaction mixture was diluted with ethyl acetate, washed with saturated ammonium chloride, water, a saturated sodium chloride solution and dried over sodium sulfate. The organic layer was concentrated, and the crude product was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 12 g, 0% to 100% ethyl acetate/hexanes) to afford (S)-2-[4-(2-chloro-6-fluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-cyclohexyl-N-(1-methyl-1H-pyrazol-3-yl)-propionamide (68 mg, 45%): 1H NMR (300 MHz, DMSO-d6) δ ppm 0.60-1.36 (m, 6H) 1.42-1.91 (m, 7H) 3.73 (s, 3H) 4.25 (d, J=18.7 Hz, 1H) 4.62 (d, J=18.7 Hz, 1H) 4.90 (dd, J=10.3, 5.4 Hz, 1H) 4.96 (s, 1H) 6.40 (d, J=2.1 Hz, 1H) 7.38-7.54 (m, 3H) 7.55 (d, J=2.1 Hz, 1H) 10.74 (s, 1H). HR-ES-MS m/z calculated for C23H26ClFN4O3 [M+Na]+ 483.1569, observed 483.1568.