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R.S. Upadhayaya et al. / European Journal of Medicinal Chemistry 39 (2004) 579–592
1-yl-propan-2-ol (7g). Compound 7g was obtained as oil in
10% yield. H-NMR d (ppm): 2.51–2.62 (m, 4H); 2.83 (t,
1H); 4.73 (s, 2H); 5.94 (brs, 1H); 6.21–6.57 (m, 3H); 6.90–
6.96 (m, 2H); 7.95–8.00 (m, 1H); 8.06 (s, 1H); 8.16 (s, 1H).
MS: m/z 564 (M + 1). Anal. (C24H25Cl2F2N9O): C, H, N.
1
2H); 3.02 (t, 2H); 3.34–3.41 (m, 4H); 4.16 (d, 1H); 4.54 (d,
1H); 4.75 (s, 2H); 5.95 (brs, 1H); 6.20 (d, 2H); 6.75 (d, 2H);
6.92–6.97 (m, 2H); 7.94–8.01 (m, 1H); 8.04 (s, 1H); 8.14 (s,
1H). MS: m/z 529 (M + 1), 531 (M + 3). Anal.
(C24H26ClF2N9O): C, H, N.
5.1.5.21.
2-(2,4-Difluorophenyl)-1-(5-{2-[4-(2-pyridyl)-
piperazin-1-yl]-ethyl}-tetrazol-2-yl)-3-[1,2,4]-triazol-1-yl-
propan-2-ol (6k). Compound 6k was obtained as oil in 45%
1
yield. H-NMR d (ppm): 2.50–2.66 (m, 4H); 2.86 (t, 2H);
5.1.5.15. 2-(2,4-Difluorophenyl)-1-(5-{2-[4-benzyl-pipera-
zin-1-yl]-ethyl}-tetrazol-2-yl)-3-[1,2,4]-triazol-1-yl-propan-
2-ol (6h). Compound 6h was obtained as oil in 46% yield.
1H-NMR d (ppm): 2.59–2.64 (m, 4H); 2.84 (t, 2H); 3.12 (t,
2H); 3.40–3.45 (m, 4H); 3.52 (s, 2H); 4.22 (d, 1H); 4.54 (d,
1H); 4.70 (s, 2H); 5.92 (s, 1H); 6.28–6.55 (m, 5H); 6.92–6.98
(m, 2H); 7.95–8.03 (m, 1H); 8.08 (s, 1H); 8.19 (s, 1H). MS:
m/z 510 (M + 1). Anal. (C25H29F2N9O): C, H, N.
3.14 (t, 2H); 3.42–3.48 (m, 4H); 4.22 (d, 1H); 4.56 (d, 1H);
4.66 (s, 2H); 6.00 (brs, 1H); 6.28–8.04 (m, 7H); 8.10 (s, 1H);
8.24 (s, 1H). MS: m/z 497 (M + 1). Anal. (C23H26F2N10O): C,
H, N.
5.1.5.22.
2-(2,4-Difluorophenyl)-1-(5-{2-[4-(2-pyridyl)-
piperazin-1-yl]-ethyl}-tetrazol-1-yl)-3-[1,2,4]-triazol-1-yl-
propan-2-ol (7k). Compound 7k was obtained as oil in 8%
1
yield. H-NMR d (ppm): 2.57–2.62 (m, 4H); 2.78 (t, 2H);
5.1.5.16. 2-(2,4-Difluorophenyl)-1-(5-{2-[4-benzyl-pipera-
zin-1-yl]-ethyl}-tetrazol-1-yl)-3-[1,2,4]-triazol-1-yl-propan-
2-ol (7h). Compound 7h was obtained as oil in 10% yield.
1H-NMR d (ppm): 2.52–2.65 (m, 4H); 2.80 (t, 2H); 3.05 (t,
2H); 3.40–3.44 (m, 4H); 3.53 (s, 2H); 4.15 (d, 1H); 4.50 (d,
1H); 4.80 (s, 2H); 6.00 (brs, 1H); 6.28–6.50 (m, 5H); 6.90–
6.95 (m, 2H); 7.95–8.02 (m, 1H); 8.05 (s, 1H); 8.15 (s, 1H).
MS: m/z 510 (M + 1). Anal. (C25H29F2N9O): C, H, N.
3.11 (t, 2H); 3.32–3.38 (m, 4H); 4.19 (d, 1H); 4.56 (d, 1H);
4.70 (s, 2H); 5.95 (brs, 1H); 6.30–8.00 (m, 7H); 8.05 (s, 1H);
8.20 (s, 1H). MS: m/z 497 (M + 1). Anal. (C23H26F2N10O): C,
H, N.
5.1.5.23. 2-(2,4-Difluorophenyl)-1-(5-{2-[4-(diphenylmethyl)-
piperazin-1-yl]-ethyl}-tetrazol-2-yl)-3-[1,2,4]-triazol-1-yl-
propan-2-ol (6l). Compound 6l was obtained as oil in 42%
1
yield. H-NMR d (ppm): 2.60–2.67 (m, 4H); 2.82 (t, 2H);
5.1.5.17. 2-(2,4-Difluorophenyl)-1-(5-{2-[4-(4-fluorophe-
nyl)-piperazin-1-yl]-ethyl}-tetrazol-2-yl)-3-[1,2,4]-triazol-
1-yl-propan-2-ol (6i). Compound 6i was obtained as oil in
3.13 (t, 2H); 3.41–3.45 (m, 4H); 4.20 (d, 1H); 4.24 (s, 1H);
4.58 (d, 1H); 4.68 (s, 2H); 5.95 (brs, 1H); 6.24–6.50 (m,
10H); 6.90–6.97 (m, 2H); 8.00–8.05 (m, 1H); 8.08 (s, 1H);
8.21 (s, 1H). MS: m/z 586 (M + 1). Anal. (C31H33F2N9O): C,
H, N.
1
50% yield. H-NMR d (ppm): 2.57–2.65 (m, 4H); 2.82 (t,
2H); 3.10 (t, 2H); 3.40–3.44 (m, 4H); 4.20 (d, 1H); 4.56 (d,
1H); 4.68 (s, 2H); 5.85 (brs, 1H); 6.25 (d, 2H); 6.60 (d, 2H);
6.93–6.98 (m, 2H); 7.99–8.04 (m, 1H); 8.10 (s, 1H); 8.20 (s,
1H). MS: m/z 514 (M + 1). Anal. (C24H26F3N9O): C, H, N.
5.1.5.24. 2-(2,4-Difluorophenyl)-1-(5-{2-[4-(diphenylmethyl)-
piperazin-1-yl]-ethyl}-tetrazol-1-yl)-3-[1,2,4]-triazol-1-yl-
propan-2-ol (7l). Compound 7l was obtained as oil in 9%
1
5.1.5.18. 2-(2,4-Difluorophenyl)-1-(5-{2-[4-(4-fluorophe-
nyl)-piperazin-1-yl]-ethyl}-tetrazol-1-yl)-3-[1,2,4]-triazol-
1-yl-propan-2-ol (7i). Compound 7i was obtained as oil in
9% yield. 1H-NMR d (ppm): 2.57–2.65 (m, 4H); 2.83 (t, 2H);
3.05 (t, 2H); 3.34–3.40 (m, 4H); 4.18 (d, 1H); 4.56 (d, 1H);
4.81 (s, 2H); 5.85 (brs, 1H); 6.25 (d, 2H); 6.63 (d, 2H);
6.90–6.97 (m, 2H); 7.99–8.03 (m, 1H); 8.06 (s, 1H); 8.22 (s,
1H). MS: m/z 514 (M + 1). Anal. (C24H26F3N9O): C, H, N.
yield. H-NMR d (ppm): 2.58–2.64 (m, 4H); 2.85 (t, 2H);
3.02 (t, 2H); 3.30–3.42 (m, 4H); 4.14 (d, 1H); 4.24 (s, 1H);
4.56 (d, 1H); 4.80 (s, 2H); 5.80 (brs, 1H); 6.22–6.56 (m,
10H); 6.90–6.97 (m, 2H); 8.01–8.05 (m, 1H); 8.06 (s, 1H);
8.20 (s, 1H). MS: m/z 586 (M + 1). Anal. (C31H33F2N9O): C,
H, N.
5.1.5.25. 2-(2,4-Difluorophenyl)-1-(5-{2-[4-(2-n-butoxyphe-
nyl)-piperazin-1-yl]-ethyl}-tetrazol-2-yl)-3-[1,2,4]-triazol-
1-yl-propan-2-ol (6m). Compound 6m was obtained as oil in
5.1.5.19. 2-(2,4-Difluorophenyl)-1-(5-{2-[4-(2,4-dichlorophe-
nyl)-piperazin-1-yl]-ethyl}-tetrazol-2-yl)-3-[1,2,4]-triazol-
1-yl-propan-2-ol (6j). Compound 6j was obtained as oil in
1
42% yield. H-NMR d (ppm): 0.95 (t, 3H); 1.72–1.77 (m,
4H); 2.60–2.67 (m, 4H); 2.85 (t, 2H); 3.10 (t, 2H); 3.40–3.46
(m, 4H); 4.05–4.10 (m, 2H); 4.20 (d, 1H); 4.58 (d, 1H); 4.68
(s, 2H); 5.90 (brs, 1H); 6.22–6.53 (m, 4H); 6.94–7.00 (m,
2H); 7.98–8.03 (m, 1H); 8.10 (s, 1H); 8.22 (s, 1H). MS: m/z
568 (M + 1). Anal. (C28H35F2N9O): C, H, N.
1
44% yield. H-NMR d (ppm): 2.57–2.65 (m, 4H); 2.83 (t,
2H); 3.12 (t, 2H); 3.40–3.44 (m, 4H); 4.22 (d, 1H); 4.55 (d,
1H); 4.66 (s, 2H); 5.80 (brs, 1H); 6.21–6.58 (m, 3H); 6.90–
6.98 (m, 2H); 7.97–8.03 (m, 1H); 8.10 (s, 1H); 8.22 (s, 1H).
MS: m/z 564 (M + 1). Anal. (C24H25Cl2F2N9O): C, H, N.
5.1.5.26. 2-(2,4-Difluorophenyl)-1-(5-{2-[4-(2-n-butoxyphe-
nyl)-piperazin-1-yl]-ethyl}-tetrazol-1-yl)-3-[1,2,4]-triazol-
1-yl-propan-2-ol (7m). Compound 7m was obtained as oil in
5.1.5.20. 2-(2,4-Difluorophenyl)-1-(5-{2-[4-(2,4-dichloro-
phenyl)-piperazin-1-yl]-ethyl}-tetrazol-1-yl)-3-[1,2,4]-tria-
zol-1-yl-propan-2-ol (7j). Compound 7j was obtained as oil
in 7% yield. 1H-NMR d (ppm): 2.52–2.62 (m, 4H); 2.77 (t,
2H); 3.05 (t, 2H); 3.33–3.41 (m, 4H); 4.12 (d, 1H); 4.56 (d,
1
11% yield. H-NMR d (ppm): 0.96 (t, 3H); 1.70–1.75 (m,
4H); 2.58–2.67 (m, 4H); 2.77 (t, 2H); 3.08 (t, 2H); 3.38–3.41
(m, 4H); 4.05–4.10 (m, 2H); 4.15 (d, 1H); 4.50 (d, 1H); 4.77