Water → 1-([1,1'-biphenyl]-2-yl)-3-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzyl)urea

A solution of 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetyl azide (0.100 g, 0.258 mmol) in acetonitrile (1.25 mL) was heated to 80° C. for 2.5 hours. The resulting solution was cooled to room temperature and [1,1′-biphenyl]-2-amine (0.0479 g, 0.283 mmol) and cesium carbonate (0.0920 g, 0.283 mmol) were added as solids. An additional amount of acetonitrile (1.0 mL) was added and the reaction was allowed to stir for 18 hours at room temperature. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated. The resulting residue was purified by flash chromatography using 0-80% ethyl acetate/B, where B=1:1 dichloromethane/hexanes to afford the title compound as a white solid (0.039 g, 28%): 1H NMR (400 MHz, DMSO-d6) δ 9.40 (s, 1H), 8.12-8.04 (m, 4H), 7.90 (dd, J=8.2, 1.2 Hz, 1H), 7.63 (dq, J=9.0, 0.9 Hz, 2H), 7.55-7.46 (m, 3H), 7.45-7.36 (m, 5H), 7.33-7.26 (m, 1H), 7.18 (dd, J=7.6, 1.7 Hz, 1H), 7.14-7.06 (m, 2H), 4.32 (d, J=5.8 Hz, 2H); 19F NMR (376 MHz, DMSO-d6) δ −56.96; ESIMS m/z 530 ([M+H]+).

1. extractionextracted with ethyl acetate (3×25 mL)
2. dry with materialThe combined organic layers were dried over magnesium sulfate
3. filtrationfiltered
4. concentrationconcentrated
5. customThe resulting residue was purified by flash chromatography

ORD 기록

ord-bb565127acc04a7f88d8f88e6acd1d6d

출처 데이터셋

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09445594B2