E. Blom et al.
purification. N-{2-[4-(2-Methoxyphenyl)piperazin-1-yl]ethyl}pyridine- 45.9. 19F NMR (376 MHz, CDCl3, 251C) d = À133.6 (m, 2F), À157.1
2-amine (WAY-100634) was prepared as described previously.40 N-{3- (m, 1F). ESI-MS: m/z 471 [M1H]1.
Chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6 -[5-({[2-(methylsulfonyl)ethyl]-
amino}methyl) - 2-furyl]quinazolin-4-amine (Lapatinib) was supplied
by GlaxoSmithKline.
Conclusion
Methyl(pentafluorophenyl)amine41 (13): Hexafluorobenzene
(5.035 g, 27.1 mmol) was dissolved in 40 mL propan-2-ol,
18/19F Exchange reactions were examined in various organo-
fluorine compounds, and the effect of solvent, temperature,
and methylamine (2.5 mL, 40% in H2O) was added. The reaction
conventional vs microwave heating, degree of fluorine load and
mixture was heated at 851C for 56 h, and then distilled
the presence of activating and deactivating groups on the
under reduced pressure to yield 13 as a colourless liquid
radiochemical yield was investigated. This study aimed to
1
(1.403 g, 26%). H NMR (CDCl3, 400 MHz, 251C) d = 3.05 (m, 3H).
understand the impact of fluorinated compounds in choosing
a labelling strategy, considering issues such as activated leaving
13C NMR (CDCl3, 100 MHz, 251C) d = 145.7 (m), 139.2 (m), 136.8
(m), 134.5 (m), 33.3 (m). 19F NMR (DMSO-d6, 376 MHz, 251C)
groups, matrix-supported substrates, catalysts, and work-up
protocols.
d = À161.5 (m, 2F), À166.0 (m, 2F), À176.6 (m, 1F). ESI-MS: m/z
198 [M1H]1.
N-(Pentafluorophenyl)benzamide42 (17): Pentafluoroaniline
Acknowledgement
(3.008 g, 16.4 mmol) was dissolved in 15 mL dry CH2Cl2 and
benzoyl chloride (3.458 g, 24.6 mmol) was added dropwise over
10 min. The mixture was stirred at room temperature for 16 h
under a nitrogen atmosphere, and then diluted with CHCl3,
washed with H2O, and concentrated under reduced pressure.
The residue was recrystallized from CHCl3/petroleum ether to
yield 17 as white crystals (0.280 g, 6%). M.p. 179–1801C. 1H NMR
(DMSO-d6, 400 MHz, 251C) d = 10.54 (bs, 1H), 8.03–7.98 (m, 2H),
7.69–7.63 (m, 1H), 7.60–7.54 (m, 2H). 13C NMR (DMSO-d6,
100 MHz, 251C) d = 165.4, 144.2 (m), 141.8 (m), 138.5 (m), 136.0
(m), 132.5, 132.3, 128.7, 127.9. 19F NMR (DMSO-d6, 376 MHz,
251C) d = À144.9 (m, 2F), À157.0 (m, 1F), À163.0 (m, 2F). ESI-MS:
m/z 288 [M1H]1.
Financial support from The Swedish Science Research Council
(BL) and the Juvenile Diabetes Research Foundation (JDRF) is
gratefully acknowledged. This work was conducted in collabora-
tion with Imanet, GE Healthcare.
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