C. Sørum et al.
Drying over MgSO4 and concentration in vacuum yielded 1.83 g
(7.06 mmol, 98%) of a yellow solid, mp 248–249 ◦C (Ref. [14]
248–249 ◦C). 1H NMR corresponded well with the reported data.[8]
1H NMR (400 MHz, DMSO-d6) δ: 12.90 (s, 1H), 8.55 (s, 1H), 7.95
(m, 2H), 7.06 (m, 2H), 6.96 (d, J = 2.1, 1H), 3.82 (s, 3H). 13C
NMR (100 MHz, DMSO-d6) δ: 160.0, 153.0, 150.0, 149.2, 140.5,
This yielded 187 mg, (0.54 mmol, 78%) of a slightly yellowish solid,
mp 290–292 ◦C, HRMS (ESI, m/z): 349.1460 (calcd C20H18FN4O+,
M+H+, 349.1459). Synthesis of 9c: Synthesis was performed
as described for 9b starting with 5 (97 mg, 0.37 mmol), 3-
fluorobenzylamine (7c) (140 mg, 1.12 mmol). This yielded 98 mg
(0.28 mmol, 76%) of an off-white solid, mp 284–285 ◦C, HRMS (ESI,
m/z): 349.1455 (calcd C20H18FN4O+, M+H+, 349.1459). Synthesis
of 9d: Synthesis was performed as described for 9b, starting
with 5 (186 mg, 0.72 mmol) and 2-fluorobenzylamine 7d (270 mg,
2.16 mmol) This yielded 183 mg (0.53 mmol, 73%) of an off-
white solid, mp 234–235 ◦C, HRMS (ESI, m/z): 349.1452 (calcd
C20H18FN4O+, M+H+, 349.1459).
127.5 (2C), 122.7, 118.0, 114.5 (2C), 94.0, 55.3. Synthesis of 8a[8,15]
:
Under an argon atmosphere, compound 5 (275 mg, 1.06 mmol),
1-butanol (3.5 mL) and (R)-1-phenylethanamine (6a) (486 mg,
4.01 mmol) were mixed and reacted at 145 ◦C for 24 h. Upon
cooling the reaction mixture to 20 ◦C, a precipitate was formed,
which was isolated by filtration and washed with diethyl ether
(25 mL). T◦his yielded 260 mg (0.75 mmol, 71%) of a white solid, mp
218–220 C, [α]2D2 = −353.3 (c = 0.11, DMSO), HRMS (ESI, m/z):
m/z 345.1715 (calcd C21H21N4O+, M+H+, 345.1710). Synthesis of
8b[8]: Synthesis was performed as described for 8a, starting with 5
(142 mg, 0.55 mmol), and (R)-1-(4-fluorophenyl)ethanamine (6b)
(308 mg, 2.22 mmol). This yielde◦d 133 mg (0.37 mmol, 67%) of
an off-white solid, mp 234–236 C, [α]2D2 = −315.9 (c = 0.16,
DMSO), HRMS (ESI, m/z): m/z 363.1630 (calcd C21H20FN4O+,
M+H+, 363.1616). Synthesis of 8c: Synthesis was performed
as described for 8a, starting with 5 (229 mg, 0.88 mmol) and
(R)-(3-fluorophenyl)ethanamine (6c) (431 mg, 3.10 mmol). This
yielded 236 mg (0.65 mmol, 74%) of a slight yellowish solid,
mp 235–236 ◦C, [α]2D2 = −347.3 (c = 0.13, DMSO), HRMS (ESI,
m/z): 363.1613 (calc. C21H20FN4O+, M+H+, 363.1616). Synthesis
of 8d: Synthesis was performed as described for 8a, starting with
5 (186 mg, 0.72 mmol) and (R)-(2-fluorophenyl)ethanamine (6d)
(401 mg, 2.88 mmol). This yielde◦d 183 mg (0.50 mmol, 70%) of
an off-white solid, mp 217–219 C, [α]2D2 = −375.9 (c = 0.13,
DMSO), HRMS (ESI, m/z): 363.1615 (calcd C21H20FN4O+, M+H+,
363.1616). Synthesis of 9b: Compound 5 (178 mg, 0.69 mmol),
4-fluorobenzylamine (7b) (198 mg, 1.51 mmol) and 1-butanol
(3.0 mL) were mixed and reacted at 145 ◦C under an argon
atmosphere for 24 h. Upon cooling the reaction mixture to 20 ◦C,
a precipitate was formed, which was isolated by filtration and
washed with diethyl ether (15 mL). The material obtained was
suspended in saturated K2CO3 (20 mL) and extracted with EtOAc
(3 × 25 mL). The combined organic fraction was washed with
brine (20 mL), dried over MgSO4 and concentrated in vacuum.
Acknowledgements
NTNU is acknowledged for use of NMR facilities and Anders Jahres
Foundation for financial support.
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c
Copyright ꢀ 2009 John Wiley & Sons, Ltd.
Magn. Reson. Chem. 2010, 48, 244–248