912
Vol. 62, No. 9
(0.143mmol). The reaction mixture was heated in the mi- (M+H)+.
crowave reactor at power 100W and 120°C for 10min. The
5-(5-(6-Cyclopentyloxypyrazin-2-yl)-2-hydroxy-
precipitate thus formed was collected by filtration. Consecu- benzylidene)thiazolidine-2,4-dione (5a): Obtained as a yellow
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tive washing with DCM (5mL×3), H2O (5mL×3), and MeOH solid in 54% yield; H-NMR (400MHz, DMSO-d6+CD3OD)
(5 mL×3) followed by drying gave the product as solid.
δ: 8.67 (1H, s), 8.21 (1H, d, J=2.0Hz), 8.10 (1H, s), 8.06–8.03
5-(3-(6-Cyclohexyloxypyrazin-2-yl)benzylidene)- (2H, m), 7.05 (1H, d, J=8.4Hz), 5.49 (1H, sext, J=4.0Hz),
thiazolidine-2,4-dione (5c): Obtained as a pale yellow solid 2.12–2.11 (2H, m), 1.78–1.76 (4H, m), 1.66–1.64 (2H, m).
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in 13% yield; H-NMR (400MHz, DMSO-d6) δ: 8.85 (1H, s), 13C-NMR (100MHz, DMSO-d6+CD3OD) δ: 168.41, 167.97,
8.38 (1H, s), 8.24 (1H, s), 8.20 (1H, d, J=8.0Hz), 7.86 (1H, s), 159.09, 147.25, 133.55, 132.13, 130.40, 127.41, 127.11, 126.42,
7.74 (1H, d, J=8.0Hz), 7.66 (1H, t, J=7.6Hz), 5.22 (1H, quint, 123.18, 120.91, 116.82, 78.39, 32.60, 23.64. ESI-MS m/z: 384
J=4.6Hz), 2.12–2.09 (2H, m), 1.81–1.78 (2H, m), 1.62–1.31 (M+H)+.
(6H, m). 13C-NMR (100MHz, DMSO-d6) δ: 168.54, 158.92,
5-(5-(6-Cyclohexyloxypyrazin-2-yl)-2-hydroxybenzylidene)-
146.97, 136.81, 135.12, 134.31, 133.30, 132.84, 131.24, 130.46, thiazolidine-2,4-dione (5b): Obtained as a yellow solid in 81%
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128.40, 127.14, 125.25, 74.23, 31.71, 25.51, 24.14. Electrospray yield; H-NMR (400MHz, DMSO-d6+CD3OD) δ: 8.68 (1H, s),
ionization-mass spectra (ESI-MS) m/z: 382 (M+H)+.
8.22 (1H, d, J=2.0Hz), 8.10 (1H, s), 8.07–8.04 (2H, m), 7.06
5-(3-(6-(2-(Dimethylamino)ethoxy)pyrazin-2-yl)- (1H, d, J=8.8Hz), 5.19 (1H, br), 2.11–2.09 (2H, m), 1.79–1.77
benzylidene)thiazolidine-2,4-dione (5e): Obtained as a pale (2H, m), 1.61–1.28 (6H, m). 13C-NMR (100MHz, DMSO-
yellow solid in 26% yield; 1H-NMR (400MHz, DMSO- d6+CD3OD) δ: 168.29, 167.94, 158.80, 147.18, 133.65, 132.23,
d6) δ: 8.90 (1H, s), 8.37 (1H, s), 8.32 (1H, s), 8.14 (1H, d, 130.37, 127.36, 127.10, 126.26, 123.06, 120.93, 116.86, 74.00,
J=6.8Hz), 7.69–7.61 (3H, m), 4.71 (2H, t, J=5.2Hz), 3.21 (2H, 31.85, 25.55, 24.30. ESI-MS m/z: 398 (M+H)+.
t, J=5.0Hz), 2.60 (6H, s). 13C-NMR (100MHz, DMSO-d6) δ:
5-(5-(6-(2-(Dimethylamino)ethoxy)pyrazin-2-yl)-2-
176.14, 172.35, 158.95, 147.58, 136.52, 135.87, 134.58, 134.07, hydroxybenzylidene)thiazolidine-2,4-dione (5d): Obtained as
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131.88, 131.12, 130.15, 128.15, 127.38, 126.52, 62.34, 56.79, an orange colored solid in 42% yield; H-NMR (400MHz,
44.55. ESI-MS m/z: 371 (M+H)+.
DMSO-d6+CD3OD) δ: 8.63 (1H, s), 8.22 (1H, d, J=1.6Hz),
5-(3-(6-(3-Dimethylamino)propoxy)pyrazin-2-yl)- 8.12 (1H, s), 8.07 (1H, s), 7.79 (1H, d, J=8.4Hz), 7.08 (1H, d,
benzylidene)thiazolidine-2,4-dione (5g): Obtained as a pale J=8.4Hz), 4.59 (2H, t, J=5.6Hz), 2.83 (2H, t, J=5.8Hz), 2.35
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yellow solid in 17% yield; H-NMR (400MHz, DMSO-d6) δ: (6H, s). 13C-NMR (100MHz, DMSO-d6+CD3OD) δ: 174.65,
8.87 (1H, s), 8.36 (1H, s), 8.28 (1H, s), 8.10 (1H, d, J=8.8Hz), 171.84, 158.88, 147.81, 133.05, 132.87, 129.42, 128.87, 127.16,
7.65–7.58 (2H, m), 7.51 (1H, s), 4.56 (2H, t, J=6.2Hz), 3.06 126.96, 122.49, 122.29, 116.65, 62.44, 57.01, 44.76. ESI-MS
(2H, t, J=7.4Hz), 2.66 (6H, s), 2.16 (2H, quint, J=6.9Hz). m/z: 387 (M+H)+.
13C-NMR (100MHz, DMSO-d6) δ: 179.38, 174.09, 159.21,
5-(5-(6-(2-(Diethylamino)ethoxy)pyrazin-2-yl)-2-
147.67, 136.40, 136.33, 134.41, 133.75, 130.99, 129.96, 127.83, hydroxybenzylidene)thiazolidine-2,4-dione (5n): Obtained as
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126.79, 124.61, 63.86, 54.94, 43.53, 24.91. ESI-MS m/z: 385 an orange colored solid in 41% yield; H-NMR (400MHz,
(M+H)+.
DMSO-d6+CDCl3) δ: 8.74 (1H, s), 8.28 (1H, d, J=2.4Hz),
5-(3-(6-((2-(Dimethylamino)ethyl)amino)pyrazin-2-yl)- 8.19 (1H, s), 8.02 (1H, dd, J=8.8, 2.4Hz), 7.89 (1H, s), 7.06
benzylidene)thiazolidine-2,4-dione (5i): Obtained as a pale (1H, d, J=8.4Hz), 4.64 (2H, t, J=5.6Hz), 3.20 (2H, m), 2.86
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yellow solid in 62% yield; H-NMR (400MHz, DMSO-d6) (4H, m), 1.09 (6H, t, J=7.2Hz). 13C-NMR (100MHz, DMSO-
δ: 8.36 (1H, s), 8.31 (1H, s), 8.03 (1H, d, J=7.6Hz), 7.99 d6+CDCl3) δ: 174.96, 171.98, 158.99, 158.94, 147.84, 133.02,
(1H, s), 7.63–7.55 (3H, m), 7.42 (1H, t, J=5.4Hz), 3.73 (2H, 132.86, 129.36, 129.09, 127.16, 126.92, 122.37, 116.64, 62.65,
q, J=5.7Hz), 3.13 (2H, t, J=6.0Hz), 2.68 (6H, s). 13C-NMR 50.94, 47.51, 10.92. ESI-MS m/z: 415 (M+H)+.
(100MHz, DMSO-d6) δ: 178.30, 173.71, 154.35, 147.81, 137.81,
5-(5-(6-(3-Dimethylamino)propoxy)pyrazin-2-yl)-2-
135.88, 133.24, 132.98, 130.71, 129.82, 128.61, 127.56, 126.90, hydroxybenzylidene)thiazolidine-2,4-dione (5f): Obtained as
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125.79, 56.81, 43.89, 36.75. ESI-MS m/z: 370 (M+H)+.
an orange colored solid in 49% yield; H-NMR (400MHz,
5-(3-(6-((3-(Dimethylamino)propyl)amino)pyrazin-2-yl)- DMSO-d6+CDCl3) δ: 8.72 (1H, s), 8.34 (1H, d, J=2.0Hz), 8.17
benzylidene(thiazolidine-2,4-dione (5k): Obtained as a pale (1H, s), 7.98 (1H, dd, J=8.4, 2.0Hz), 7.82 (1H, s), 7.03 (1H,
1
yellow solid in 26% yield; H-NMR (400MHz, DMSO-d6) d, J=8.4Hz), 4.54 (2H, t, J=6.4Hz), 2.96 (2H, t, J=7.6Hz),
δ: 8.37 (1H, s), 8.33 (1H, s), 7.99 (1H, d, J=7.6Hz), 7.93 (1H, 2.59 (6H, s), 2.13 (2H, quint, J=7.0Hz). 13C-NMR (100MHz,
s), 7.59 (1H, d, J=8.0Hz), 7.54 (1H, t, J=7.6Hz), 7.48 (1H, s), DMSO-d6+CDCl3) δ: 173.26, 172.49, 159.09, 158.88, 147.91,
7.34 (1H, t, J=5.6Hz), 3.50 (2H, q, J=6.3Hz), 2.99 (2H, t, 132.83, 132.56, 130.67, 128.85, 127.15, 126.85, 122.70, 121.16,
J=7.8Hz), 2.65 (6H, s), 1.96 (2H, quint, J=7.3Hz). 13C-NMR 116.51, 63.78, 55.09, 43.87, 25.37. ESI-MS m/z: 401 (M+H)+.
(100MHz, DMSO-d6) δ: 180.31, 174.73, 154.54, 147.83, 137.73,
5-(5-(6-(3-Diethylaminopropoxy)pyrazin-2-yl)-2-
136.24, 134.78, 132.90, 130.84, 129.68, 128.07, 127.19, 126.36, hydroxybenzylidene)thiazolidine-2,4-dione (5o): Obtained as
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124.36, 55.88, 43.42, 38.01, 25.22. ESI-MS m/z: 384 (M+H)+.
a red orange colored solid in 37% yield; H-NMR (400MHz,
5-(3-(6-(4-Methylpiperazin-1-yl)pyrazin-2-yl)benzylidene)- DMSO-d6) δ: 8.69 (1H, s), 8.34 (1H, s), 8.15 (1H, s), 7.96–7.94
thiazolidine-2,4-dione (5m): Obtained as a pale yellow solid (1H, m), 7.80 (1H, s), 7.02 (1H, d, J=8.4Hz), 4.56 (2H, t,
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in 20% yield; H-NMR (400MHz, DMSO-d6) δ: 8.52 (1H, J=6.2Hz), 3.17–3.15 (2H, m), 3.06 (4H, q, J=7.2Hz), 2.19–2.18
s), 8.36 (1H, s), 8.33 (1H, s), 8.11 (1H, d, J=7.2Hz), 7.74 (1H, (2H, m), 1.16 (6H, t, J=7.0Hz). 13C-NMR (100MHz, DMSO-
s), 7.65–7.60 (2H, m), 3.78 (4H, br), 2.73 (4H, br), 2.43 (3H, d6) δ: 174.22, 172.47, 159.03, 158.65, 147.96, 132.75, 132.58,
s). 13C-NMR (100MHz, DMSO-d6+CDCl3) δ: 172.70, 170.74, 131.68, 128.59, 127.12, 126.83, 122.86, 120.41, 116.32, 63.48,
153.96, 147.34, 137.59, 134.98, 130.96, 130.08, 129.73, 128.97, 46.73, 24.14, 21.22, 9.31. ESI-MS m/z: 429 (M+H)+.
128.63, 128.16, 127.76, 53.97, 45.26, 43.59. ESI-MS m/z: 382
5-(5-(6-((2-Dimethylamino)ethyl)amino)pyrazin-2-yl)-2-