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Y. Kotaiah et al. / European Journal of Medicinal Chemistry 75 (2014) 195e202
4.4.1. N-(4-Chlorophenyl)-5-methyl-6-(3-phenyl-[1,2,4]triazolo
[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d]pyrimidin-4-amine
(10a)
4.4.6. N-(3-Chloro-4-fluorophenyl)-5-methyl-6-(3-phenyl-[1,2,4]
triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d]pyrimidin-
4-amine (10f)
Yield 71%; Pale yellow solid, m.p. ¼ 246e248 ꢂC; IR (KBr)
n
(cme
2.96 (s,
Yield 74%; Off-White solid, m.p. ¼ 228e230 ꢂC; IR (KBr)
n
1): 3438, 2937, 1605, 1538; 1H NMR (DMSO-d6, 400 MHz)
d
(cmꢀ1): 3442, 2923, 1607, 1547; 1H NMR (DMSO-d6, 400 MHz)
3H, selenopheneeCH3), 7.46 (d, 2H, AreH, J ¼ 8.0 Hz), 7.57e7.68 (m,
d 3.00 (s, 3H, selenopheneeCH3), 6.58e6.90 (m, 5H, Phenyl), 7.45 (t,
5H, Phenyl), 8.26 (d, 2H, AreH, J ¼ 8.0 Hz), 8.49 (s,1H, NeH), 8.91 (s,
1H, AreH, J ¼ 8.0 Hz), 7.63 (dd, 1H, AreH, J ¼ 4.0 Hz), 7.89 (dd, 1H,
1H, CeH), 13C NMR (DMSO-d6, 100 MHz):
d 18.05, 120.84, 124.30,
AreH, J ¼ 8.0 Hz), 8.28 (s, 1H, NeH), 8.51 (s, 1H, CeH), 13C NMR
125.46, 125.81, 128.39, 129.18, 129.79, 130.38, 137.76, 137.89, 140.58,
147.16, 151.95, 154.09, 157.15, 161.42, and 166.20; LCeMS (positive
ion mode): m/z 524 (M þ H)þ for C22H14ClN7SSe.
(DMSO-d6, 100 MHz): d 18.13, 115.83, 116.05, 118.17, 120.91, 121.28,
123.87, 124.08, 127.11, 129.70, 132.22, 136.39, 137.13, 140.08, 143.84,
147.48, 153.60, 155.52, 157.71 and 162.04; LCeMS (positive ion
mode): m/z 542 (M þ H)þ for C22H13ClFN7SSe.
4.4.2. N-(4-Chlorophenyl)-5-methyl-6-(3-p-tolyl-[1,2,4]triazolo
[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d]pyrimidin-4-amine
(10b)
4.4.7. N-(3-Chloro-4-fluorophenyl)-5-methyl-6-(3-p-tolyl-[1,2,4]
triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d]pyrimidin-
4-amine (10g)
Yield 68%; Off-white solid, m.p. ¼ 240e242 ꢂC; IR (KBr)
n
Yield 82%; Brown solid, m.p. ¼ 272e274 ꢂC; IR (KBr)
n
(cmꢀ1):
d 2.41 (s, 3H,
(cmꢀ1): 3437, 2922, 1603, 1543; 1H NMR (DMSO-d6, 400 MHz)
3412, 2936, 1608, 1546; 1H NMR (DMSO-d6, 400 MHz)
d
2.41 (s, 3H, PhenyleCH3), 2.98 (s, 3H, selenopheneeCH3), 7.39 (d,
PhenyleCH3), 3.00 (s, 3H, selenopheneeCH3), 7.39 (t, 1H, AreH,
J ¼ 8.0 Hz), 7.42 (dd, 1H, AreH, J ¼ 4.0 Hz), 7.53 (dd, 1H, AreH,
J ¼ 8.0 Hz), 7.86 (d, 2H, AreH, J ¼ 8.0 Hz), 8.15 (d, 2H, AreH,
J ¼ 8.0 Hz), 8.40 (s, 1H, NeH), 9.18 (s, 1H, CeH), 13C NMR (DMSO-d6,
2H, AreH, J ¼ 8.0 Hz), 7.46 (d, 2H, AreH, J ¼ 8.0 Hz), 7.68 (d, 2H, Are
H, J ¼ 8.0 Hz), 8.16 (d, 2H, AreH, J ¼ 8.0 Hz), 8.41 (s, 1H, NeH), 8.50
(s, 1H, CeH), 13C NMR (DMSO-d6, 100 MHz):
d 18.23, 20.96, 117.81,
123.04, 125.77, 126.60, 127.38, 129.52, 129.92, 131.43, 137.07, 137.46,
141.26, 148.50, 152.03, 153.14, 156.84, 162.10, and 167.48; LCeMS
(positive ion mode): m/z 538 (M þ H)þ for C23H16ClN7SSe.
100 MHz):
d 18.14, 21.01, 116.36, 116.57, 119.30, 120.17, 121.40,
123.34, 124.46, 125.70, 129.68, 129.97, 131.14, 137.10, 138.87, 141.22,
145.66, 147.87, 152.28, 154.13, 158.76 and 161.48; LCeMS (positive
ion mode): m/z 556 (M þ H)þ for C23H15ClFN7SSe.
4.4.3. N-(4-Chlorophenyl)-6-(3-(4-methoxyphenyl)-[1,2,4]triazolo
[3,4-b][1,3,4]thiadiazol-6-yl)-5-methylselenopheno[2,3-d]
pyrimidin-4-amine (10c)
4.4.8. N-(3-Chloro-4-fluorophenyl)-6-(3-(4-methoxyphenyl)-
[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl)-5-methylselenopheno
[2,3-d]pyrimidin-4-amine (10h)
Yield 74%; Off-white solid, m.p. ¼ 262e264 ꢂC; IR (KBr)
n
(cmꢀ1):
2.90 (s, 3H,
3448, 2928, 1657, 1543; 1H NMR (DMSO-d6, 400 MHz)
d
Yield 76%; Pale yellow solid, m.p. ¼ 262e264 ꢂC; IR (KBr)
n
selenopheneeCH3), 3.79 (s, 3H, PhenyleOCH3), 7.13 (d, 2H, AreH,
J ¼ 8.0 Hz), 7.36 (d, 2H, AreH, J ¼ 8.0 Hz), 7.59 (d, 2H, AreH,
J ¼ 8.0 Hz), 8.11 (d, 2H, AreH, J ¼ 8.0 Hz), 8.41 (s, 1H, NeH), 8.91 (s,
(cmꢀ1): 3446, 3150, 2836,1610,1547; 1H NMR (DMSO-d6, 400 MHz)
d
2.98 (s, 3H, selenopheneeCH3), 3.86 (s, 3H, PhenyleOCH3), 7.21 (d,
2H, AreH, J ¼ 8.0 Hz), 7.46 (t,1H, AreH, J ¼ 8.0 Hz), 7.61 (dd,1H, Are
H, J ¼ 4.0 Hz), 7.90 (dd, 1H, AreH, J ¼ 8.0 Hz), 8.21 (d, 2H, AreH,
J ¼ 8.0 Hz), 8.52 (s, 1H, NeH), 8.91 (s, 1H, CeH), 13C NMR (DMSO-d6,
1H, CeH), 13C NMR (DMSO-d6, 100 MHz):
d 17.68, 56.80, 116.53,
121.39, 125.12, 125.98, 128.31, 129.14, 130.44, 131.68, 136.24, 138.72,
140.80, 149.02, 151.37, 154.40, 156.81, 162.94, and 168.22; LCeMS
(positive ion mode): m/z 554 (M þ H)þ for C23H16ClN7OSSe.
100 MHz):
d 18.06, 52.98, 113.84, 117.40, 121.72, 123.61, 128.17,
119.20, 120.83, 121.62, 122.80, 124.07, 125.22, 129.41, 130.18, 131.77,
137.21, 138.29, 140.85, 144.38, 147.20, 153.12, 156.24, 157.68 and
162.07; LCeMS (positive ion mode): m/z 572 (M þ H)þ for
4.4.4. 4-(6-(4-(4-Chlorophenylamino)-5-methylselenopheno[2,3-d]
pyrimidin-6-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl)phenol
(10d)
C23H15ClFN7OSSe.
4.4.9. 4-(6-(4-(3-Chloro-4-fluorophenylamino)-5-
methylselenopheno[2,3-d]pyrimidin-6-yl)-[1,2,4]triazolo[3,4-b]
[1,3,4]thiadiazol-3-yl)phenol (10i)
Yield 62%; White solid, m.p. ¼ 242e244 ꢂC; IR (KBr)
n
(cmꢀ1):
2.99
3512, 3425, 2922, 1604, 1566; 1H NMR (DMSO-d6, 400 MHz)
d
(s, 3H, selenopheneeCH3), 6.24 (s, 1H, PhenyleOH), 7.44 (d, 2H, Are
H, J ¼ 8.0 Hz), 7.70 (d, 2H, AreH, J ¼ 8.0 Hz), 8.22 (d, 2H, AreH,
J ¼ 8.0 Hz), 8.48 (d, 2H, AreH, J ¼ 8.0 Hz), 8.51 (s, 1H, NeH), 9.17 (s,
Yield 69%; White solid, m.p. ¼ 225e227 ꢂC; IR (KBr)
n
(cmꢀ1):
2.99
3394, 3158, 2948, 1609, 1570; 1H NMR (DMSO-d6, 400 MHz)
d
(s, 3H, selenopheneeCH3), 5.99 (br s, 1H, PhenyleOH), 7.22 (t, 1H,
AreH, J ¼ 8.0 Hz), 7.44 (d, 2H, AreH, J ¼ 8.0 Hz), 7.62 (dd, 1H, AreH,
J ¼ 4.0 Hz), 7.92 (dd, 1H, AreH, J ¼ 8.0 Hz), 8.24 (d, 2H, AreH,
J ¼ 8.0 Hz), 8.52 (s, 1H, NeH), 9.12 (s, 1H, CeH), 13C NMR (DMSO-d6,
1H, CeH), 13C NMR (DMSO-d6, 100 MHz):
d 18.13, 120.76, 124.45,
127.39, 127.87, 128.36, 129.67, 131.43, 132.05, 137.76, 138.06, 140.26,
148.84, 153.14, 153.57, 157.63, 161.08, and 167.40; LCeMS (positive
ion mode): m/z 539 (M þ H)þ for C22H14ClN7OSSe.
100 MHz):
d 18.13, 116.40, 116.62, 118.76, 120.73, 121.08, 123.48,
124.64, 127.31, 135.93, 137.90, 142.68, 146.94, 149.27, 153.06, 153.70,
155.00,157.04 161.22 and 166.52; LCeMS (positive ion mode): m/z
558 (M þ H)þ for C22H13ClFN7OSSe.
4.4.5. N-(4-Chlorophenyl)-5-methyl-6-(3-(4-nitrophenyl)-[1,2,4]
triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d]pyrimidin-
4-amine (10e)
Yield 68%; Yellow solid, m.p. ¼ 226e228 ꢂC; IR (KBr)
n
(cmꢀ1):
d 2.97 (s, 3H,
4.4.10. N-(3-Chloro-4-fluorophenyl)-5-methyl-6-(3-(4-
nitrophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl)
selenopheno[2,3-d]pyrimidin-4-amine (10j)
3436, 2912, 1607, 1547; 1H NMR (DMSO-d6, 400 MHz)
selenopheneeCH3), 6.74 (d, 2H, AreH, J ¼ 8.0 Hz) 7.45 (d, 2H, AreH,
J ¼ 8.0 Hz), 7.68 (d, 2H, AreH, J ¼ 8.0 Hz), 7.93 (d, 2H, AreH,
J ¼ 8.0 Hz), 8.50 (s, 1H, NeH), 9.08 (s, 1H, CeH), 13C NMR (DMSO-d6,
Yield 61%; Yellow solid, m.p. ¼ 236e238 ꢂC; IR (KBr)
n
(cmꢀ1):
d 2.93 (s, 3H,
3206, 2957, 1602, 1576; 1H NMR (DMSO-d6, 400 MHz)
100 MHz):
d
18.04, 112.19, 113.58, 120.89, 124.21, 124.45, 127.08,
selenopheneꢀCH3), 7.26 (t, 1H, AreH, J ¼ 8.0 Hz), 7.38 (d, 2H, AreH,
J ¼ 8.0 Hz), 7.58 (dd, 1H, AreH, J ¼ 4.0 Hz), 8.03 (dd, 1H, AreH,
J ¼ 8.0 Hz), 8.16 (d, 2H, AreH, J ¼ 8.0 Hz), 8.79 (s, 1H, NeH), 9.01 (s,
127.62, 128.32, 137.58, 137.80, 139.27, 141.92, 147.17, 150.93, 153.97,
156.99 and 172.09; LCeMS (positive ion mode): m/z 569 (M þ H)þ
for C22H13ClN8O2SSe.
1H, CeH), 13C NMR (DMSO-d6, 100 MHz):
d 18.24, 115.84, 116.40,