Molecules 2019, 24, 1609
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1.91 (m, 4H, CHaliph), 1.73 (m, 4H, CHaliph). 13C NMR (101 MHz, DMSO)
δ
154.37 (Ar), 148.39 (Ar),
143.82 (Ar), 141.36 (Ar), 130.85 (Ar), 124.30 (Ar), 118.65 (Ar), 115.45 (Ar, Ar) 114.88 (Ar, Ar), 111.31 (Ar),
56.98 (Coxy), 55.70 (Ctriaz), 51.03 (Cpip, Cpip), 47.31 (Cpip, Cpip), 45.27 (Cpip), 28.44 (Caliph), 26.50–25.58
(Caliph), 23.31 (Caliph), 13.96 (Caliph). FT-IR 3002 (C–H Ar, Str), 2939, 2840 (C–HAliph, Str), 1708 (C=O,
Str), 1640 (C=N, Str), 1541, 1509 (C=C, Str), 1374 (C–N, Str), 1260, 1025 (C–O, Str). HPLC 92% (tR =
1.40), Rf = 0.65, yield = 27%, mp = 144–146 ◦C.
2-[6-[4-(2-ethoxyphenyl)piperazin-1-yl]hexyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride (10m): 1H
NMR (300 MHz, CDCl3)
δ 8.20–8.15 (s, 1H, ArH), 7.77 (d, J = 7.1 Hz, 1H, ArH), 7.43 (m, 1H, ArH),
7.08 (dd, J = 15.7, 4.7 Hz, 4H, ArH), 6.51 (s, 1H, ArH), 4.96 (m, 2H, OCH), 4.45 (m, 2H, CHNCO), 4.33
(t, J = 7.3 Hz, 2H, CHpip), 4.02 (t, J = 6.9 Hz, 2H, CHpip), 3.61 (t, J = 13.0 Hz, 4H, CHpip), 3.13 (s, 2H,
CHaliph), 1.89 (m, 4H, CHaliph), 1.64 (t, J = 7.0 Hz, 3H, CHaliph), 1.44 (m, 4H, CHaliph). 13C NMR (101
MHz, DMSO)
δ 155.67 (Ar), 147.23 (Ar), 144.81 (Ar), 139.45 (Ar), 137.84 (Ar), 120.12 (Ar), 120.01 (Ar),
116.42 (Ar, Ar), 112.98 (Ar, Ar), 110.31 (Ar), 58.91 (Coxy), 55.74 (Ctriaz), 50.04 (Cpip, Cpip), 48.21 (Cpip
,
Cpip), 44.18 (Cpip), 29.60 (Caliph), 26.12 (Caliph), 21.13 (Caliph), 13.90 (Caliph), 13.40 (Caliph). FT-IR 2990
(C–H Ar, Str), 2936; 2860 (C–HAliph, Str), 1701 (C=O, Str), 1636 (C=N, Str), 1541, 1491 (C=C, Str), 1356
(C–N, Str), 1251, 1040 (C–O, Str). HPLC 97% (tR = 1.63), Rf = 0.46, yield = 31%, mp = 143–145 ◦C.
1
2-[6-[4-(2-pyridyl)piperazin-1-yl]hexyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride (10n): H NMR
(300 MHz, DMSO)
δ 8.14 (d, J = 4.1 Hz, 1H, ArH), 7.83 (t, J = 7.0 Hz, 2H, ArH), 7.22 (d, J = 3.2 Hz,
2H, ArH), 7.15 (d, J = 8.9 Hz, 1H, ArH), 6.88 (s, 1H, ArH), 6.67–6.57 (m, 1H, ArH), 4.40 (d, J = 13.8 Hz,
2H, CHNCO), 3.88 (dd, J = 16.3, 9.5 Hz, 2H, CHpip), 3.58 (d, J = 11.6 Hz, 2H, CHpip), 3.37 (d, J = 14.1
Hz, 2H, CHpip), 3.22 (s, 2H, CHpip), 3.08 (s, 2H, CHaliph), 1.75 (d, J = 6.8 Hz, 4H, CHaliph), 1.28 (d, J =
27.2 Hz, 4H, CHaliph). 13C NMR (101 MHz, DMSO)
δ 148.38 (Ar), 141.35 (Ar), 130.85 (Ar, Ar), 124.30
(Ar, Ar), 115.44 (Ar), 114.27 (Ar, Ar), 114.16 (Ar), 111.31 (Ar), 55.80 (Ctriaz), 50.29 (Cpip), 45.27 (Cpip),
43.34 (Cpip), 42.34 (Cpip), 28.44 (Caliph), 26.02 (Caliph), 25.88 (Caliph), 23.28 (Caliph). FT-IR 2970 (C–H Ar,
Str), 2936, 2861 (C–HAliph, Str), 1701 (C=O, Str), 1633 (C=N, Str), 1536, 1495 (C=C, Str), 1365 (C–N, Str).
HPLC 98% (tR = 2.32), m/z = 381.27, Rf = 0.48, yield = 70%, mp = 175–178 ◦C.
1
2-[6-(4-pyrimidin-2-ylpiperazin-1-yl)hexyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride (10o): H NMR
(300 MHz, CDCl3) δ 8.61 (d, J = 5.2 Hz, 1H, ArH), 8.29 (s, 1H, ArH), 7.76 (s, 1H, ArH), 7.10 (s, 2H, ArH),
6.99 (s, 1H, ArH), 6.54–6.50 (m, 1H, ArH), 4.28–4.21 (m, 2H, CHNCO), 4.01 (s, 4H, CHpip), 3.70 (s, 4H,
CHpip), 3.07–3.00 (m, 2H, CHaliph), 1.95–1.81 (m, 4H, CHaliph), 1.45–1.38 (m, 4H, CHAliph). 13C NMR
(75 MHz, CDCl3) δ 157.67 (Ar), 148.81 (Ar), 141.73 (Ar), 130.08 (Ar), 123.96 (Ar), 115.59 (Ar), 111.38 (Ar),
110.82 (Ar), 109.87 (Ar), 57.58 (Ctriaz), 51.54 (Cpip, Cpip), 45.57 (Cpip, Cpip), 41.78 (Cpip), 29.56 (Caliph),
28.11 (Caliph), 26.16 (Caliph), 23.54 (Caliph). FT-IR 3023 (C–H Ar, Str), 2937, 2857 (C–HAliph, Str), 1700
(C=O, Str), 1616 (C=N, Str), 1540 (C=C, Str), 1350 (C–N, Str). HPLC 90%, (tR = 1.42), Rf = 0.35, yield =
45% (Samsung), yield = 61% (CEM Discover SP reactor), mp = 146–148 ◦C.
2-[6-(4-phenylpiperazin-1-yl)hexyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride (10p): 1H NMR
(300 MHz, DMSO)
δ 7.84 (d, J = 7.0 Hz, 1H, ArH), 7.25 (dd, J = 14.6, 5.8 Hz, 4H, ArH), 7.00 (d,
J = 8.1 Hz, 2H, ArH), 6.86 (t, J = 7.2 Hz, 1H, ArH), 6.61 (dd, J = 8.4, 5.8 Hz, 1H, ArH), 3.77 (t, J = 12.0 Hz,
2H, CHNCO), 3.64–3.35 (m, 4H, CHpip), 3.16 (dd, J = 22.3, 9.6 Hz, 4H, CHpip), 3.06 (m, 2H, CHaliph),
1.74 (m, 4H, CHaliph), 1.32 (m, 4H, CHaliph). FT-IR 2987 (C–H Ar, Str), 2937, 2861 (C–HAliph, Str), 1693
(C=O, Str), 1639 (C=N, Str), 1541, 1491 (C=C, Str), 1375 (C–N, Str). HPLC 90% (tR = 3.69), m/z = 380.27,
Rf = 0.58, yield = 55%, mp = 133–137 ◦C.
1
2-[6-[4-(2-phenylphenyl)piperazin-1-yl]hexyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one hydrochloride (10r): H NMR
(300 MHz, CDCl3)
δ 7.76 (d, J = 7.2 Hz, CH-, 1H, ArH), 7.52 (d, J = 7.2 Hz, 2H, ArH), 7.42 (t, J = 7.5 Hz,
2H, ArH), 7.37–7.29 (m, 2H, ArH), 7.24–7.22 (m, 1H, ArH), 7.21–7.13 (m, 2H, ArH), 7.09 (d, J = 3.2 Hz,
2H, ArH), 6.54–6.46 (m, 1H, ArH), 3.99 (t, J = 7.0 Hz, 2H, CHNCO), 3.53 (t, J = 12.0 Hz, 2H, CHpip), 3.35
(d, J = 10.9 Hz, 2H, CHpip), 3.10 (d, J = 13.4 Hz, 2H, CHpip), 2.86 (m, 2H, CHpip), 2.69 (m, 2H, CHaliph),
1.81 (m, 4H, CHaliph), 1.39 (m, 4H, CHaliph). 13C NMR (101 MHz, DMSO)
δ 148.71 (Ar), 148.37 (Ar),