1378
L. Yin, F. Erdmann, and J. Liebscher
Vol. 42
13
%, mp 70-1 °C. 1H nmr (CDCl ), δ (ppm): 1.67 (m, 2 H, CH ),
3 2
7.81 (s, 1H, H-5), 8.05-8.08 (m, 4 H, Ph-H); C nmr (CDCl ), δ
3
2.12 (s, 3 H, 2 x CH ), 2.19 (t, 2 H, J = 7.2 Hz, CH ), 2.49 (t, 2 H,
(ppm): 26.5 CH , 37.5 CH , 45.6 CH , 59. 6 CH , 110.0 CH(C-
5), 127.3 CH, 128.9 CH, 130.6 CH, 137.6 C, 164.7 C, 171.3 C;
HRMS (EI) calcd for C H N (M ) 317.1892, found 317.1890.
Catalytic hydrogenation of 2d and 2e gave 1c in 45 % and 49
% yield, respectively. The expected chlorophenyl-containing
products were not observed.
3
2
2
2
3
2
J = 7.7 Hz, CH ), 7.01 (dd, 1 H, J = 9.0 Hz, J =1.5 Hz , H-7),
2
1
2
13
+
7.16-7.58 (m, 11 H, Ph-H and H-8), 7.67 (s, 1 H, H-5); C nmr
21 23
3
(CDCl ), δ (ppm): 28.7 CH , 30.4 CH , 45.4 CH , 58.7 CH ,
3
2
2
3
2
117.9 CH, 120.8 CH, 126.3 C, 126.9 CH, 127.3 CH, 128.0 CH,
128.2 CH, 128.8 Ch, 129.5 CH, 130.1 C,130.7 CH,132.2 C,
134.3 C, 142.4 C, 142.4 C, 144.1 C; HRMS (EI) calcd for
[3-(5,6-Diphenylpyrazin-2-yl)-propyl]-dimethyl-amine (1f).
+
C H N (M ) 355.2049, found 355.2045.
24 25
3
The residue was purified by column chromatography on neu-
[3-(2,3-Diphenylimidazo[1,2-b]pyridazin-6-yl)-propyl]-
dimethyl-amine (1k).
tral Al O eluting with EtOAc/MeOH (10:1). The compound 1f
2
3
1
was obtained as a light brown oil, yield 58 %. H nmr (CDCl ), δ
(ppm): 1.89-1.99 (m, 2 H, CH ), 2.18 (s, 6 H, 2 _ CH ), 2.32 (t,
3
Purification by column chromatography on neutral Al O ,
2
3
2
3
eluting with EtOAc/MeOH (10:1) gave a light brown solid, yield
2H, J = 7.3 Hz, CH ), 2.86 (t, 2 H, J = 7.7Hz, CH ),7.20-7.36 (m,
2
2
1
73 %, mp 112-3 °C. H nmr (CDCl ), δ (ppm): 1.80 (m, 2 H,
13
3
10 H, Ph-H), 8.40 (s, 1 H, H-3); C nmr (CDCl ), δ (ppm): 27.3
CH , 32.8 CH , 45.5 CH , 59.1 CH , 128.2 CH, 128.3 CH, 128.5
3
CH ), 2.11 (s, 6H, 2 x CH ), 2.23 (t, 2 H, J = 7.3 Hz, CH ), 2,73
2
3
2
2
2
3
2
(t, 2 H, J = 7.7 Hz, CH ), 6.85 (d, 1 H, J = 9.1 Hz, H-7), 7.19-7.60
2
CH, 129.6 CH, 129.7 CH, 138.8 C, 138.9 C, 141.6 CH(C-3),
13
(m, 10H, Ph-H), 7.79 (d, 1 H, J = 9.1 Hz, H-8); C nmr (CDCl ),
+
3
150.0 C, 151.6 C, 154.5 C; HRMS (EI) calcd for C H N (M )
21 23
3
δ ( ppm): 26.6 CH , 33.3 CH , 45.5 CH , 58.9 CH , 118.5 CH,
2
2
3
2
317.1892, found 317.1890.
[3-(2,5-Diphenyl-oxazol-4-yl)-propyl]-dimethyl-amine (1g).
Purification by column chromatography on neutral Al O elut-
124.9 CH, 127.7 CH, 128.3 CH, 128.3 CH, 128.4 CH, 128.4 CH,
129.1 C, 130.5 CH,134.4 C, 137.9 C, 142.9 C, 154.9 C.
Anal. Calcd. for C H N (356.46): C, 77.50; H, 6.79; N,
23 24
4
2
3
15.72. Found: C, 77.52; H, 6.82; N, 15.62.
ing with cyclohexane/EtOAc (1:1) gave a light yellow oil, yield
1
58 %. H nmr (CDCl ), δ (ppm): 1.78-1.88 (m, 2 H, CH ), 2.09
[3-(9-Benzyl-6-phenyl-purin-8-yl)-propyl]-dimethyl-amine (1l).
3
2
(s, 6 H, 2 x CH ), 2.25 (t, 2 H, J = 7.4 Hz, CH ), 2.70 (t, 2 H, J =
7.7 Hz, CH ), 7.17-7.95 (m, 10 H, Ph-H); C nmr (CDCl ), δ
(ppm): 25.1 CH , 26.8 CH , 45.5 CH , 59.2 CH , 125.6 CH,
3
2
Purification by column chromatography on neutral Al O elut-
2
3
13
2
3
ing with cyclohexane/EtOAc (1:1) gave a light yellow solid,
2
2
3
2
1
yield 70 %, mp 81-3 °C. H nmr (CDCl ), δ (ppm): 1.94-2.02 (m,
3
126.3 CH, 127.6 C, 127.7 CH, 128.7 CH, 128.8 CH, 129.1 C,
2 H, CH ), 2.13 (s, 6 H, 2 x CH ), 2.27 (t, 2H, J = 7.2 Hz, CH ),
2
3
2
130.1 CH, , 133.1 C, 137.5 C, 145.4 C, 159.5 C; HRMS (EI)
2.82 (t, 2 H, J = 7.4 Hz, CH ), 5.45 (s, 2H, CH ), 7.07-8.78 (m,
2
2
+
calcd for C H N O (M ) 306.1173, found 306.1173.
20 22
2
13
10 H, Ph-H), 8.91 (s, 1H, H-2); C nmr (CDCl ), δ (ppm): 25.0
3
Dimethyl-[3-(3-methyl-1,5-diphenyl-pyrazol-4-yl)-propyl]-
CH , 25.5 CH , 45.4 CH , 45.5 CH , 58.7 CH , 126.9 CH, 128.1
2 2 3 2 2
amine (1h).
CH, 128.6 CH, 129.0 C, 129.7 CH, 130.6 CH, 130.9 C, 132.2 C,
135.8 C, 151.8 CH(H-2), 152.9 C, 154.1 C, 157.4 C.
Purification by column chromatography on neutral Al O elut-
2
3
Anal. Calcd for C H N (371.48): C, 74.36; H, 6.78; N,
23 21
5
ing with EtOAc/MeOH (10:1) gave a light brown oil, yield 76 %.
18.85. Found: C, 74.56; H, 6.91; N, 18.77
1
H nmr (CDCl ), δ (ppm): 1.48-1.58 (m, 2 H, CH ), 2.06 (s, 3 H,
3
3
2
CH ), 2.12 (t, 2 H, J = 7.4 Hz, CH ), 2.28 (s, 3 H, CH ), 2.37 (t,
N’-(2,3-Diphenylpyrido[2,3-b]pyrazin-7-yl)-N,N-dimethyl-
propane-1,3-diamine (1m).
2
3
13
2 H, J = 7.9 Hz, CH ), 7.07-7.62 (m,10 H, Ph-H); C nmr
2
(CDCl ), δ (ppm): 12.2 CH , 21.3 CH , 28.9 CH , 45.4 CH , 59.
3
3
2
2
3
Purification by column chromatography on neutral Al O elut-
2
3
4 CH , 119.4 C, 124.4 CH, 126.3 CH, 128.1 CH, 128.4 CH,
2
ing with EtOAc/MeOH (10:1), gave a light brown oil, yield 54
128.6, 129.8 CH, 131.1 C, 140.1 C, 140.4 C, 148.3 C; HRMS
1
%. H nmr (CDCl ), δ (ppm): 1.85-1.92 (m, 2 H, CH ), 2.18 (s, 6
3
2
+
(EI) calcd for C H N (M ) 319.2049, found 319.2046.
21 25
3
H; 2 x CH ), 2.30 (t, 2 H, J = 7.2 Hz, CH ), 2.88 (t, 2 H, J = 7.2
3
2
Anal. Calcd. for C H N (319.44): C, 78.96; H, 7.89; N,
21 25
3
Hz, CH ), 7.26-7.30 (m, 6 H, Ph-H), 7.46 (m, 2 H, Ph-H), 7.51
2
13.15. Found: C, 78.83; H, 8.02; N, 13.07.
(m, 2 H, Ph-H), 8.2 (d, 1 H, J = 2.3 Hz, H-8), 8.96 (d, 1 H, J
6,8
6,8
13
= 2.3 Hz, H-6); C nmr (CDCl ), δ (ppm): 28.7 CH , 30.7 CH ,
[3-(1-Benzyl-4,5-diphenyl-imidazol-2-yl)-propyl]-dimethyl-
amine (1i).
3
2
2
45.4 CH , 58. 7 CH , 128.1 CH, 128.4 CH, 129.2, CH, 129.2 CH,
3
2
129.8 CH, 130.2 CH, 135.8 CH(C-8), 136.0 C, 138.2 C, 138.7 C,
Purification by column chromatography on neutral Al O eluting
2
3
140.2 C, 148.4 C, 154.5 C, 155.3 C, 155.8 CH(C-6); HRMS (EI)
1
with EtOAc gave a light brown oil, yield 63 %. H nmr (CDCl ), δ
(ppm): 1.92-2.02 (m, 2 H, CH ), 2.19 (s, 6 H, 2 x CH ), 2,35 (t, 2 H,
3
+
calcd for C H N (M ) 368.2001, found 368.2001.
24 24
4
2
3
J = 7.8 Hz, CH ), 2,70 (t, 2 H, J = 7.58 Hz, CH ), 5.01 (s, 2 H,
Acknowledgement.
2
2
13
CH ), 6.92-7.52 (m, 15 H, Ph-H). C nmr (CDCl ), δ (ppm): 25.1
2
3
We thank Martina Heidler for excellent technical assistance.
We gratefully acknowledge financial support by Deutsche
Forschungsgemeinschaft, Fonds der Chemischen Industrie and
Elbion AG Radebeul.
CH , 26.0 CH , 45.3 CH , 46.8 CH , 59.1 CH , 125.8 CH, 126.1
2
2
3
2
2
CH, 126.7 CH, 127.5 CH, 128.1 C, 128.5 CH, 128. 8 CH, 128.9
CH, 131.0 CH, 132.4 C, 134.8 C, 136.7 C, 137.4 C, 148.3; HRMS
+
(EI) calcd for C H N (M ) 395.2362, found 395.2359.
27 29
3
[3-(2,3-Diphenylimidazo[1,2-a]pyridin-6-yl)-propyl]-dimethyl-
amine (1j).
REFERENCES AND NOTES
Purification by column chromatography on neutral Al O elut-
[1] R. J. Stratta, Clin. Transplant., 13, 1 (1999).
2
3
ing with AcOEt/MeOH (10:1) gave a light brown solid, yield 47
[2] Y. F. Vanrenterghem, Curr. Opin. Nephrol. Hy., 8, 669 (1999).