574 Csuk et al.
Arch. Pharm. Pharm. Med. Chem. 2004, 337, 571−578
CH2(4Ј)), 1.97Ϫ1.88 (m, 2H, CH2(2Ј)), 1.71Ϫ1.63 (m, 2H,
(OCF3). MS (ESI, 4.1 kV, 8 µL/min, N2, methanol): 378 (4%)
[(M-Boc)H]+, 422 (12%) [(M-ibutene)H]+, 478 (100%) [MH]+.
Analysis for C25H30F3N3O3 (477.53): C 62.88; H 6.33; N 8.80;
found: C 62.71; H 6.43; N 8.75.
t
CH2(3Ј)), 1.43 (s, 9H, Bu). 13C NMR (100 MHz, CDCl3): δ =
156.2 (quart.), 155.3 (C=O), 143.5 (quart.), 140.7 (quart.),
139.3 (quart.), 133.2 (CH), 127.1 (CH), 124.6 (CH), 123.1
1
(CH), 122.6 (CH), 120.5 (q, JC,F = 258.6 Hz, OCF3), 120.4
(CH), 116.6 (CH), 112.6 (quart.), 112.3 (quart.), 79.2 (quart.,
tBu), 48.3 (CH2(1Ј)), 39.9 (CH2(4Ј)), 28.4 (CH3, Bu), 27.4
t
tert-Butyl N-{7-[9-(2-trifluoromethoxyacridinyl)amino]heptyl}
carbamate (14)
(CH2), 27.2 (CH2). 19F NMR (188 MHz, CDCl3): δ = Ϫ58.7
(OCF3). MS (ESI, 4.1 kV, 8 µL/min, N2, methanol): 394 (14%)
[(M-ibutene)H]+, 450 (100%) [MH]+. Analysis for
C23H26F3N3O3 (449.48): C 61.46; H 5.83; N 9.35; found: C
61.32; H 5.99; N 9.21.
As described for 9, from 1 (2.0 g, 6.7 mmol), phenol (10.0 g,
0.1 mol) and 7 (1.70 g, 7.4 mmol), 14 (1.59 g, 48%) was
obtained as a red, highly viscous oil. UV-vis (methanol): λmax
(log ε) = 286 nm (4.71). IR (film): ν = 3425s, 2930s, 2856s,
1690s, 1632s, 1591s, 1566s, 1528s, 1502s, 1391m, 1365m,
tert-Butyl N-{5-[9-(2-trifluoromethoxyacridinyl)amino]pentyl}
carbamate (12)
1276m, 1247s, 1170s, 1030m cmϪ1
.
1H NMR (400 MHz,
3
CDCl3): δ = 8.09 (d, JH,H = 9.55 Hz, 1H, H-C(4)), 8.06 (d,
3
As described for 9, from 1 (2.0 g, 6.7 mmol), phenol (10.0 g,
0.1 mol) and 5 (1.49 g, 7.4 mmol), 12 (2.12 g, 68%) was
obtained as a red, highly viscous oil. UV-vis (methanol): λmax
(log ε) = 282 nm (4.69). IR (film): ν = 3439s, 2934w, 1630m,
3JH,H = 8.72 Hz, 1H, H-C(8)), 8.03 (d, JH,H = 8.72 Hz, 1H,
4
H-C(5)), 7.92 (d, JH,H = 2.08 Hz, 1H, H-C(1)), 7.68 (dd,
3
3JH,H = 8.72 Hz, JH,H = 6.64 Hz, 1H, H-C(6)), 7.52 (dd,
4
3JH,H = 9.55 Hz, JH,H = 2.08 Hz, 1H, H-C(3)), 7.41 (dd,
1508w, 1367w, 1261s, 1218m, 1165m cmϪ1
.
1H NMR (400
3JH,H = 8.72 Hz, JH,H = 6.64 Hz, 1H, H-C(7)), 5.00 (br s,
3
3
MHz, CDCl3): δ = 8.07 (d, JH,H = 9.55 Hz, 1H, H-C(4)), 8.05
1H, NH), 4.47 (br s, 1H, NH), 3.80Ϫ3.75 (m, 2H, CH2(1Ј)),
3.11Ϫ3.03 (m, 2H, CH2(7Ј)), 1.81Ϫ1.73 (m, 2H, CH2(2Ј)),
(d, 3JH,H = 8.72 Hz, 1H, H-C(8)), 8.03 (d, 3JH,H = 8.72 Hz, 1H,
4
t
H-C(5)), 7.92 (d, JH,H = 2.08 Hz, 1H, H-C(1)), 7.67 (dd,
1.47Ϫ1.25 (m, 17H, Bu, 4 ϫ CH2(3ЈϪ6Ј)). 13C NMR (100
3
3JH,H = 8.72 Hz, JH,H = 6.64 Hz, 1H, H-C(6)), 7.51 (dd,
MHz, CDCl3): δ = 155.9 (C=O), 151.2 (quart.), 149.3 (quart.),
4
3JH,H = 9.55 Hz, JH,H = 2.08 Hz, 1H, H-C(3)), 7.40 (dd,
147.7 (quart.), 144.0 (quart.), 131.9 (CH), 130.1 (CH), 129.8
3
1
3JH,H = 8.72 Hz, JH,H = 6.64 Hz, 1H, H-C(7)), 5.05 (br s,
(CH), 124.4 (CH), 123.9 (CH), 121.8 (CH), 120.5 (q, JC,F
=
1H, NH), 4.53 (br s, 1H, NH), 3.79Ϫ3.74 (m, 2H, CH2(1Ј)),
3.15Ϫ3.08 (m, 2H, CH2(5Ј)), 1.84Ϫ1.76 (m, 2H, CH2(2Ј)),
256.4 Hz, OCF3), 116.7 (quart.), 115.9 (quart.), 113.8 (CH),
t
79.0 (quart., Bu), 50.8 (CH2(1Ј)), 40.5 (CH2(7Ј)), 31.7 (CH2),
t
t
1.54Ϫ1.42 (m, 4H, 2 ϫ CH2(3Ј,4Ј)), 1.41 (s, 9H, Bu). 13C
30.0 (CH2), 29.0 (CH2), 28.5 (CH3, Bu), 26.8 (CH2), 26.6
NMR (100 MHz, CDCl3): δ = 155.9 (C=O), 151.2 (quart.),
149.1 (quart.), 147.5 (quart.), 144.0 (quart.), 131.6 (CH),
130.1 (CH), 129.4 (CH), 124.4 (CH), 123.9 (CH), 121.9 (CH),
(CH2). 19F NMR (188 MHz, CDCl3): δ = Ϫ58.5 (OCF3). MS
(ESI, 4.1 kV, 8 µL/min, N2, methanol): 392 (8%) [(M-Boc)H]+,
436 (15%) [(M-ibutene)H]+, 492 (100%) [MH]+. Analysis for
C26H32F3N3O3 (491.56): C 63.53; H 6.56; N 8.55; found: C
63.41; H 6.71; N 8.39.
1
120.5 (q, JC,F = 256.6 Hz, OCF3), 116.7 (quart.), 115.9
t
(quart.), 113.9 (CH), 79.2 (quart., Bu), 50.7 (CH2(1Ј)), 40.2
(CH2(5Ј)), 31.3 (CH2), 29.9 (CH2), 28.4 (CH3, tBu), 24.1
(CH2). 19F NMR (188 MHz, CDCl3): δ = Ϫ58.5 (OCF3). MS
(ESI, 4.1 kV, 8 µL/min, N2, methanol): 408 (12%) [(M-
ibutene)H]+, 464 (100%) [MH]+. Analysis for C24H28F3N3O3
(463.50): C 62.19; H 6.09; N 9.07; found: C 62.00; H 6.23;
N 8.95.
tert-Butyl
N-{8-[9-(2-trifluoromethoxyacridinyl)amino]octyl}
carbamate (15)
As described for 9, from 1 (2.0 g, 6.7 mmol), phenol (10.0 g,
0.1 mol) and 8 (2.71 g, 11.1 mmol), 15 (3.09 g, 61%) was
obtained as a red, highly viscous oil. UV-vis (methanol): λmax
(log ε) = 286 nm (4.76). IR (film): ν = 3346m, 2930s, 2857m,
1694s, 1633m, 1564s, 1520s, 1392m, 1366s, 1255s, 1165s,
tert-Butyl
N-{6-[9-(2-trifluoromethoxyacridinyl)amino]hexyl}
carbamate (13)
As described for 9, from 1 (2.0 g, 6.7 mmol), phenol (10.0 g,
0.1 mol) and 6 (1.60 g, 7.4 mmol), 13 (1.24 g, 39%) was
obtained as a red, highly viscous oil. UV-vis (methanol): λmax
(log ε) = 287 nm (4.70). IR (film): ν = 3358m, 3009m, 2934s,
2860m, 1692s, 1619m, 1561s, 1509s, 1476s, 1392s, 1366s,
1041m cmϪ1. 1H NMR (400 MHz, CDCl3): δ = 8.05 (d, 3JH,H
9.55 Hz, 1H, H-C(4)), 8.03 (d, JH,H = 8.72 Hz, 1H, H-C(8)),
=
3
3
4
8.02 (d, JH,H = 8.72 Hz, 1H, H-C(5)), 7.92 (d, JH,H = 2.08
3
3
Hz, 1H, H-C(1)), 7.65 (dd, JH,H = 8.72 Hz, JH,H = 6.64 Hz,
1H, H-C(6)), 7.50 (dd, JH,H = 9.55 Hz, JH,H = 2.08 Hz, 1H,
H-C(3)), 7.38 (dd, JH,H = 8.72 Hz, JH,H = 6.64 Hz, 1H, H-
C(7)), 4.49 (br s, 1H, NH), 3.80Ϫ3.75 (m, 2H, CH2(1Ј)),
3.10Ϫ3.03 (m, 2H, CH2(8Ј)), 1.82Ϫ1.74 (m, 2H, CH2(2Ј)),
3
4
1
3
3
1258s, 1167s, 1022m cmϪ1. H NMR (400 MHz, CDCl3): δ =
3
3
8.08 (d, JH,H = 9.55 Hz, 1H, H-C(4)), 8.06 (d, JH,H = 8.72
3
Hz, 1H, H-C(8)), 8.05 (d, JH,H = 8.72 Hz, 1H, H-C(5)), 7.94
(s, 1H, H-C(1)), 7.67 (dd, JH,H = 8.72 Hz, JH,H = 6.64 Hz,
1H, H-C(6)), 7.51 (dd, JH,H = 9.55 Hz, JH,H = 2.08 Hz, 1H,
H-C(3)), 7.39 (dd, JH,H = 8.72 Hz, JH,H = 6.64 Hz, 1H, H-
C(7)), 5.15 (br s, 1H, NH), 4.51 (br s, 1H, NH), 3.79Ϫ3.74
(m, 2H, CH2(1Ј)), 3.13Ϫ3.05 (m, 2H, CH2(6Ј)), 1.81Ϫ1.73 (m,
3
3
t
1.46Ϫ1.38 (m, 13H, Bu, 2 ϫ CH2(3Ј,7Ј)), 1.33Ϫ1.23 (m, 6H,
3
4
3
CH2(4Ј,5Ј,6Ј)). 13C NMR (100 MHz, CDCl3): δ = 155.9
3
3
(C=O), 151.2 (quart.), 149.3 (quart.), 147.6 (quart.), 144.0
(quart.), 131.8 (CH), 130.1 (CH), 129.7 (CH), 124.5 (CH),
1
123.9 (CH), 121.8 (CH), 120.7 (q, JC,F = 256.7 Hz, OCF3),
t
t
2H, CH2(2Ј)), 1.50Ϫ1.32 (m, 15H, Bu, 3 ϫ CH2(3Ј,4Ј,5Ј)).
116.7 (quart.), 115.9 (quart.), 113.8 (CH), 79.0 (quart., Bu),
13C NMR (100 MHz, CDCl3): δ = 155.9 (C=O), 151.2 (quart.),
149.2 (quart.), 147.5 (quart.), 143.9 (quart.), 131.6 (CH),
130.2 (CH), 129.5 (CH), 124.4 (CH), 123.8 (CH), 121.9 (CH),
50.8 (CH2(1Ј)), 40.6 (CH2(8Ј)), 31.7 (CH2), 30.1 (CH2), 29.2
t
(CH2), 29.1 (CH2), 28.5 (CH3, Bu), 26.8 (CH2), 26.7 (CH2).
19F NMR (188 MHz, CDCl3): δ = Ϫ58.5 (OCF3). MS (ESI, 4.1
kV, 8 µL/min, N2, methanol): 406 (4%) [(M-Boc)H]+, 450
(10%) [(M-ibutene)H]+, 506 (100%) [MH]+. Analysis for
C28H34F3N3O3 (517.60): C 64.98; H 6.62; N 8.12; found: C
64.81; H 6.85; N 7.99.
1
120.6 (q, JC,F = 254.6 Hz, OCF3), 116.8 (quart.), 115.8
t
(quart.), 113.9 (CH), 79.1 (quart., Bu), 50.5 (CH2(1Ј)), 40.2
(CH2(6Ј)), 31.6 (CH2), 30.1 (CH2), 28.5 (CH3, tBu), 26.4
(CH2), 26.3 (CH2). 19F NMR (188 MHz, CDCl3): δ = Ϫ58.5
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