A. Carotti et al.
MED
1H), 4.29 (t, J=5.8 Hz, 2H), 4.17 (t, J=5.8 Hz, 2H), 3.79 (s, 9H),
1.96–2.01 ppm (m, 4H), 1 OH not detected; ESIMS m/z: 452 [M]+.
3-Hydroxy-N,N,N-trimethyl-5-{4-[(2-oxo-2H-chromen-3-yl)oxy]bu-
toxy}benzenaminium iodide (12T): Prepared by following general
procedure F, starting from amine 12 (0.026 g, 0.070 mmol). Treat-
ment with Et2O yielded a white solid (0.031 g, 87%): 1H NMR
(300 MHz, [D6]acetone): d=9.90 (s, 1H, dis. with D2O), 7.57–7.60
(m, 1H), 7.41–7.47 (m, 1H), 7.28–7.32 (m, 4H), 6.96–6.99 (m, 1H),
6.67–6.68 (m, 1H), 4.19–4.20 (m, 4H), 3.79 (s, 9H), 2.00–2.03 ppm
(m, 4H); ESIMS m/z: 384 [M]+.
3-{4-[(3-Chloro-4-methyl-2-oxo-2H-chromen-7-yl)oxy]butoxy}-5-
hydroxy-N,N,N-trimethylbenzenaminium iodide (7T): Prepared
by following general procedure F, starting from amine 7 (0.029 g,
0.070 mmol). Treatment with Et2O yielded a white solid (0.036 g,
93%): 1H NMR (300 MHz, [D6]acetone): d=7.77 (d, J=8.8 Hz, 1H),
7.38–7.39 (m, 1H), 7.02 (dd, J1 =2.5 Hz, J2 =8.8 Hz, 1H), 6.93–6.95
(m, 2H), 6.64–6.66 (m, 1H), 4.25 (t, J=5.8 Hz, 2H), 4.17 (t, J=
5.8 Hz, 2H), 3.78 (s, 9H), 2.59 (s, 3H), 2.01–2.04 ppm (m, 4H), 1 OH
not detected; ESIMS m/z: 432 (100) [M]+, 434 (36).
3-{4-[(6,7-Dimethoxy-2-oxo-2H-chromen-3-yl)oxy]butoxy}-5-hy-
droxy-N,N,N-trimethylbenzenaminium iodide (13T): Prepared by
following general procedure F, starting from amine 13 (0.030 g,
0.070 mmol). Treatment with Et2O yielded a white solid (0.037 g,
92%): 1H NMR (300 MHz, [D6]acetone): d=7.31 (t, J=2.5 Hz, 1H),
7.25 (s, 1H), 7.13 (s, 1H), 6.96 (t, J=2.5 Hz, 1H), 6.92 (s, 1H), 6.69 (t,
J=2.5 Hz, 1H), 4.12–4.20 (m, 4H), 3.89 (s, 3H), 3.84 (s, 3H), 3.79 (s,
9H), 1.99–2.01 ppm (m, 4H), 1 OH not detected; ESIMS m/z: 444
[M]+.
3-({5-[(3-Chloro-4-methyl-2-oxo-2H-chromen-7-yl)oxy]pentyl}-
oxy)-5-hydroxy-N,N,N-trimethylbenzenaminium iodide (8T): Pre-
pared by following general procedure F, starting from amine 8
(0.030 g, 0.070 mmol). Treatment with Et2O yielded a white solid
1
(0.037 g, 91%): H NMR (300 MHz, [D6]acetone): d=9.41 (s, 1H, dis.
with D2O), 7.77 (d, J=8.8 Hz, 1H), 7.15 (t, J=2.2 Hz, 1H), 7.05 (t,
J=2.2 Hz, 1H), 7.01 (dd, J1 =2.5 Hz, J2 =8.8 Hz, 1H), 6.93 (d, J=
2.5 Hz, 1H), 6.71 (t, J=2.2 Hz, 1H), 4.19 (t, J=6.3 Hz, 2H), 4.12 (t,
J=6.3 Hz, 2H), 3.84 (s, 9H), 2.59 (s, 3H), 1.85–1.98 (m, 4H), 1.66–
1.73 ppm (m, 2H); ESIMS m/z: 446 (100) [M]+, 448 (34).
3-Hydroxy-N,N,N-trimethyl-5-{4-[(2-oxo-2H-chromen-4-yl)oxy]bu-
toxy}benzenaminium iodide (14T): Prepared by following general
procedure F, starting from amine 14 (0.026 g, 0.070 mmol). Treat-
ment with Et2O yielded a yellow solid (0.033 g, 91%): 1H NMR
(300 MHz, [D6]acetone): d=7.85–7.88 (m, 1H), 7.62–7.67 (m, 1H),
7.28–7.37 (m, 2H), 7.11–7.14 (brm, 1H), 7.00–7.02 (m, 1H), 6.70–
6.72 (m, 1H), 5.78 (s, 1H), 4.39 (t, J=6.1 Hz, 2H), 4.22 (t, J=6.1 Hz,
2H), 3.80 (s, 9H), 2.09–2.17 ppm (m, 4H), 1 OH not detected; ESIMS
m/z: 384 [M]+.
3-Hydroxy-N,N,N-trimethyl-5-{4-[(6-oxo-7,8,9,10-tetrahydro-6H-
benzo[c]chromen-3-yl)oxy]butoxy}benzenaminium iodide (9T):
Prepared by following general procedure F, starting from amine 9
(0.030 g, 0.070 mmol). Treatment with Et2O yielded a yellow solid
(0.036 g, 92%): 1H NMR (300 MHz, [D6]acetone): d=7.62 (d, J=
8.8 Hz, 1H), 7.18 (t, J=1.9 Hz, 1H), 7.05 (t, J=1.9 Hz, 1H), 6.93 (dd,
J1 =2.5 Hz, J2 =8.8 Hz, 1H), 6.85 (d, J=2.5 Hz, 1H), 6.71 (t, J=
1.9 Hz, 1H), 4.18–4.21 (m, 4H), 3.84 (s, 9H), 2.46–2.48 (m, 4H),
2.01–2.03 (m, 4H), 1.77–1.85 ppm (m, 4H), 1 OH not detected;
ESIMS m/z: ESIMS m/z: 438 [M]+.
3-Hydroxy-N,N,N-trimethyl-5-{4-[(2-oxo-2H-chromen-5-yl)oxy]bu-
toxy}benzenaminium iodide (15T): Prepared by following general
procedure F, starting from amine 15 (0.026 g, 0.070 mmol). Treat-
ment with Et2O yielded a white solid (0.034 g, 95%): 1H NMR
(300 MHz, [D6]acetone): d=9.41 (s, 1H, dis. with D2O), 8.18 (d, J=
9.9 Hz, 1H), 7.54 (t, J=8.5 Hz, 1H), 7.22 (t, J=2.2 Hz, 1H), 7.08 (t,
J=2.2 Hz, 1H), 6.95 (d, J=8.5 Hz, 1H), 6.89 (d, J=8.5 Hz, 1H), 6.79
(t, J=2.2 Hz, 1H), 6.32 (d, J=9.9 Hz, 1H), 4.26–4.30 (m, 2H), 4.19–
4.23 (m, 2H), 3.84 (s, 9H), 2.01–2.04 ppm (m, 4H); ESIMS m/z: 384
[M]+.
N-Ethyl-3-hydroxy-N,N-dimethyl-5-{4-[(6-oxo-7,8,9,10-tetrahydro-
6H-benzo[c]chromen-3-yl)oxy]butoxy}benzenaminium
iodide
(9D): Prepared by following general procedure F, starting from
amine 9 (0.030 g, 0.070 mmol). Treatment with Et2O yielded a
1
white solid (0.026 g, 65%): H NMR (300 MHz, [D6]acetone): d=7.62
(d, J=8.8 Hz, 1H), 7.06–7.09 (m, 1H), 7.01–7.03 (m, 1H), 6.93 (dd,
J1 =2.5 Hz, J2 =8.8 Hz, 1H), 6.85 (d, J=2.5 Hz, 1H), 6.74–6.80 (m,
1H), 4.17–4.23 (m, 4H), 4.16 (q, J=7.2 Hz, 2H), 3.78 (s, 6H), 2.79–
2.81 (m, 2H), 2.44–2.48 (m, 2H), 1.99–2.04 (m, 4H), 1.74–1.89 (m,
4H), 1.23 ppm (t, J=7.2 Hz, 3H), 1 OH not detected; ESIMS m/z:
452 [M]+.
3-Hydroxy-N,N,N-trimethyl-5-{4-[(2-oxo-2H-chromen-8-yl)oxy]bu-
toxy}benzenaminium iodide (16T): Prepared by following general
procedure F, starting from amine 16 (0.026 g, 0.070 mmol). Treat-
ment with Et2O yielded a off-white solid (0.033 g, 93%): 1H NMR
(300 MHz, [D6]acetone): d=9.41 (s, 1H, dis. with D2O), 7.99 (d, J=
9.6 Hz, 1H), 7.21–7.34 (m, 2H), 7.16–7.20 (m, 1H), 7.12–7.14 (brm,
1H), 7.03–7.05 (m, 1H), 6.71–6.72 (m, 1H), 6.45 (d, J=9.6 Hz, 1H),
4.22–4.28 (m, 4H), 3.83 (s, 9H), 1.96–2.02 ppm (m, 4H); ESIMS m/z:
384 [M]+.
3-Hydroxy-N,N,N-trimethyl-5-{4-[(6-oxo-6H-benzo[c]chromen-3-
yl)oxy]butoxy}benzenaminium iodide (10T): Prepared by follow-
ing general procedure F, starting from amine 10 (0.029 g,
0.070 mmol). Treatment with Et2O yielded a yellow solid (0.037 g,
3-Hydroxy-N,N,N-trimethyl-5-{4-[(2-oxo-2H-chromen-6-yl)oxy]bu-
toxy}benzenaminium iodide (17T): Prepared by following general
procedure F, starting from amine 17 (0.026 g, 0.070 mmol). Treat-
ment with Et2O yielded a white solid (0.034 g, 84%): 1H NMR
(300 MHz, CD3OD): d=7.91 (d, J=9.6 Hz, 1H), 7.27–7.30 (m, 1H),
7.15–7.20 (m, 2H), 6.84–6.85 (m, 1H), 6.78–6.79 (m, 1H), 6.52–6.53
(m, 1H), 6.43 (d, J=9.6 Hz, 1H), 4.10–4.12 (m, 4H), 3.58 (s, 9H),
1.98–2.02 ppm (m, 4H); ESIMS m/z: 384 [M]+.
1
95%): H NMR (300 MHz, [D6]acetone): d=8.20–8.30 (m, 3H), 7.88–
7.93 (m, 1H), 7.58–7.63 (m, 1H), 7.37–7.39 (m, 1H), 7.11–7.18 (m,
1H), 7.02 (dd, J1 =2.5 Hz, J2 =8.8 Hz, 1H), 6.94–6.95 (m, 1H), 6.66–
6.67 (m, 1H), 4.19–4.41 (m, 4H), 3.78 (s, 9H), 1.98–2.01 ppm (m,
4H), 1 OH not detected; ESIMS m/z: 434 [M]+.
3-[(3-{[(3-Chloro-4-methyl-2-oxo-2H-chromen-7-yl)oxy]methyl}-
benzyl)oxy]-5-hydroxy-N,N,N-trimethylbenzenaminium
iodide
(11T): Prepared by following general procedure F, starting from
amine 11 (0.033 g, 0.070 mmol). Treatment with Et2O yielded a
white solid (0.038 g, 90%): H NMR (300 MHz, [D6]acetone): d=7.79
N-Ethyl-3-hydroxy-N,N-dimethyl-5-{4-[(2-oxo-2H-chromen-6-
yl)oxy]butoxy}benzenaminium iodide (17D): Prepared by follow-
ing general procedure F, starting from amine 17 (0.026 g,
1
(d, J=8.8 Hz, 1H), 7.67 (s, 1H), 7.47–7.51 (m, 3H), 7.38–7.40 (m,
1H), 7.10 (dd, J1 =2.5 Hz, J2 =8.8 Hz, 1H), 7.01–7.04 (m, 2H), 6.75–
6.76 (m, 1H), 5.33 (s, 2H), 5.21 (s, 2H), 3.78 (s, 9H), 2.59 ppm (s,
3H), 1 OH not detected; ESIMS m/z: 480 (100) [M]+, 482 (37).
0.070 mmol). Treatment with Et2O yielded a off-white solid
(0.034 g, 92%): 1H NMR (300 MHz, CD3OD): d=7.91 (d, J=9.6 Hz,
1H), 7.27–7.30 (m, 1H), 7.15–7.20 (m, 2H), 6.75–6.76 (m, 1H), 6.67–
6.70 (m, 1H), 6.52–6.54 (m, 1H), 6.43 (d, J=9.6 Hz, 1H), 4.09–4.88
1628
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ChemMedChem 2010, 5, 1616 – 1630