Triethylamine → N-(4-fluorophenyl)-N'-[3-[[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl](3,3,3-trifluoro-2-hydroxypropyl)amino]phenyl]urea

The 3-[(3-aminophenyl)[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol (50 mg, 0.12 mmol) was dissolved in 1 mL of dichloromethane. Triethylamine (20 μL, 0.14 mmol) followed by 4-fluorophenyl isocyanate (14.6 μL, 0.13 mmol) were added. The solution was stirred at room temperature for 18 hours. The reaction was filtered through pre-wetted celite eluting with ethyl acetate. The solvent was evaporated, and the residue was purified by reverse phase HPLC eluting with 10% to 90% acetonitrile in water to afford 26 mg (40%) of the desired N-(4-fluorophenyl)-N′-[3-[[[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl](3,3,3-trifluoro-2-hydroxypropyl)amino]phenyl]urea product as a yellow oil, which was greater than 95% pure by reverse phase HPLC analysis. HRMS calcd. for C25H22F8N3O3: 564.1533 [M+H]+, found: 564.1566. 1H NMR (CDCl3) δ3.7 (m, 2H), 4.1 (m, 1H), 4.7 (m, 2H), 5.9 (tt, 1H), 6.6 (d, 1H), 6.9-7.4 (m, 1H), 7.5 (s, 1H), 7.8 (s, 1H).

1. additionwere added
2. filtrationThe reaction was filtered through pre-wetted
3. washcelite eluting with ethyl acetate
4. customThe solvent was evaporated
5. customthe residue was purified by reverse phase HPLC
6. washeluting with 10% to 90% acetonitrile in water

ORD 기록

ord-38ed7830eb914a56a7fd200ca34e8d09

출처 데이터셋

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06699898B2