ACCEPTED MANUSCRIPT
A mixture of 6-arylmethyl-3-hydroxylphenyl-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one (10 mmol), substituted alkyl
chlorides (10 mmol), potassium carbonate (50 mmol), KI (1 mmol) and acetone (25 mL) was refluxed for 24h. The
solvent was evaporated, a residual solid was given and recrystallized form ethanol.
4.7.1. 6-benzyl-3-(2-(2-morpholinoethoxy)phenyl)-7H-thiazolo[3,2-b]-1,2,4-triazin-7-one (7a)
This compound was obtained as a white crystal, 39.0% yield; mp: 145-147 °C; 1H-NMR (600 MHz, DMSO-d6): δ
7.50 (1H, t, J = 8.7Hz), 7.42 (2H, d, J = 8.7Hz), 7.22 (5H, m), 7.13 (1H, d, J = 8.7Hz), 7.05 (1H, t, J = 8.7Hz), 4.00
(2H, t, J = 5.2Hz), 3.89 (2H, s), 3.40 (4H, t, J = 4.2Hz), 2.36 (2H, t, J = 5.2Hz), 2.18 (4H, t, J = 4.2Hz); EI-MS
(m/z): 56, 70, 91, 100, 111, 134, 149, 163, 192, 218, 330, 448(M)+; IR (KBr): υ 3083, 2851, 2364, 1636, 1478,
1384, 1289, 1264, 1116, 1042, 961, 857, 756, 701 cm-1; Anal. Calcd For C24H24N4O3S: C, 64.27; H, 5.39; N,12.49.
Found: C, 64.35; H, 5.35; N, 12.42.
4.7.2. 6-(4-Methoxybenzyl)-3-{2-[2-(dimethylamino)-2-oxoethoxy]phenyl}thiazolo[3,2-b]-1,2,4-triazin-7-one (7b)
This compound was obtained as a white crystal, 81.5% yield; mp: 238-239 °C; 1H-NMR (600 MHz, DMSO-d6):
δ 7.34~7.48 (3H, m), 7.12 (2H, d, J = 8.4Hz), 7.05 (2H, m), 6.79 (2H, d, J = 8.4Hz), 4.77 (2H, s), 3.80 (2H, s), 3.70
(3H, s), 2.89 (3H, s), 2.78 (3H, s); ESI-MS (m/z): 451.0 (M+H+), 472.9 (M+Na+); IR (KBr): υ 3123, 2928, 1666,
1642, 1590, 1567, 1511, 1478, 1418, 1383, 1356, 1300, 1238, 1179, 1122, 1064, 1045, 1028, 921, 849, 811, 767,
736 cm-1; Anal. Calcd For C23H22N4O4S: C, 61.32; H, 4.92; N,12.44. Found: C, 61.26; H, 4.97; N, 12.48.
4.7.3. 6-Benzyl-3-{3-methyl-4-[2-(1-piperidinyl)ethoxy]phenyl}-thiazolo[3,2-b]-1,2,4-triazin-7-one (7c)
This compound was obtained as a white crystal, 43.3% yield; mp: 168-169℃; 1H-NMR (600 MHz, DMSO-d6): δ
7.43 (1H, d, J = 7.8Hz), 7.39 (H, s), 7.36 (H, s), 7.23~7.30 (5H, m), 6.98 (1H, d, J = 8.4Hz), 4.13 (2H, s), 3.88 (2H,
s), 2.70 (2H, s), 2.46 (4H, s), 2.13 (3H, s), 1.50 (4H, br), 1.39 (2H, br); ESI-MS (m/z): 461.0 (M+H)+; IR (KBr): υ
3109, 2931, 2785, 1634, 1575, 1478, 1385, 1359, 1305, 1257, 1134, 1037, 957, 883, 859, 815, 799, 767, 750, 708
cm-1; Anal. Calcd For C26H28N4O2S: C, 67.80; H, 6.13; N,12.16. Found: C, 67.74; H, 6.17; N, 12.19.
4.7.4. 6-(4-Methoxybenzyl)-3-{3-methyl-4-[2-(1-piperidinyl)ethoxy]phenyl}thiazolo[3,2-b]-1,2,4-triazin-7-one (7d)
1
This compound was obtained as a white crystal, 82.0% yield; mp: 165-166 °C; H-NMR (600 MHz, CDCl3): δ
7.36 (1H, d, J = 9.0Hz), 7.32 (1H, s), 7.29 (2H, d, J = 8.4Hz), 6.84 (1H, d, J = 7.8Hz), 6.83 (2H, d, J = 8.4Hz), 6.68
(1H, s), 4.21 (2H, br), 4.06 (2H, s), 3.80 (3H, s), 2.90 (2H, br), 2.59 (4H, br), 2.24 (3H, s), 1.65 (4H, br), 1.48 (2H,
br); ESI-MS (m/z): 491.0 (M+H+), 981.0 (2M+H+); IR (KBr): υ 3067, 2933, 2852, 1632, 1565, 1513, 1486, 1384,
1356, 1302, 1248, 1177, 1135, 1034, 952, 863, 802, 764 cm-1; Anal. Calcd For C27H30N4O3S: C, 66.10; H, 6.16;
N,11.42. Found: C, 66.16; H, 6.12; N, 11.48.
4.7.5. 6-Benzyl-3-{4-[2-(dimethylamino)-2-oxoethoxy]phenyl}thiazolo[3,2-b]-1,2,4-triazin-7-one(7e)
This compound was obtained as a white crystal, 78.2% yield; mp: 144-146°C; ESI-MS (m/z): 421.0 (M+H)+;
1H-NMR (300 MHz, CDCl3): δ 7.47 (2H, d, J = 8.7Hz), 7.25~7.36 (5H, m), 6.98 (2H, d, J = 8.7Hz), 6.72 (1H, s),
4.77 (2H, s), 4.12 (2H, s), 3.13 (3H, s), 3.02 (3H, s) ; ESI-MS (m/z): 421.0 (M+H+) ; IR (KBr): υ 3077, 2928, 1636,
1576, 1507, 1484, 1417, 1354, 1307, 1255, 1185, 1122, 1069, 827, 755, 704 cm-1; Anal. Calcd For C22H20N4O3S: C,
62.84; H, 4.79; N,13.32. Found: C, 62.74; H, 4.82; N, 13.36.
4.7.6. 6-Benzyl-3-{4-[2-(1-piperidinyl)ethoxy]phenyl}thiazolo[3,2-b]-1,2,4-triazin-7-one (7f)
1
This compound was obtained as a white crystal, 80.5% yield; mp: 185-187 °C; H-NMR (300 MHz, CDCl3): δ
7.46 (2H, d, J = 8.8Hz), 7.25~7.36 (5H, m), 6.92 (2H, d, J = 8.8Hz), 6.72 (1H, s), 4.18 (2H, t, J = 6.0Hz), 4.12 (2H,
s), 2.83 (2H, t, J = 6.0Hz), 2.56 (4H, br), 1.65 (4H, m), 1.48 (2H, m); ESI-MS (m/z): 447.0 (M), 893.0 (2M), 915.9
(M+Na+); IR (KBr): υ 3109, 2931, 2851, 1634, 1579, 1507, 1480, 1416, 1386, 1356, 1293, 1253, 1173, 1036, 933,
824, 767 cm-1; Anal. Calcd For C25H26N4O2S: C, 67.24; H, 5.87; N,12.55. Found: C, 67.34; H, 5.82; N, 12.51.
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