R. Chikhale et al. / European Journal of Medicinal Chemistry 96 (2015) 30e46
35
1645, 1600, 1540, 1500 cmꢁ1 (aromatic ring). 1H NMR (400 MHz,
DMSO) 2.48 (s, 3H, CH3), 4.32 (s, 2H, NeH), 5.36 (s, 1H, Pyrimi-
m.p. 230e232 ꢀC. IR (KBr)
n
¼ 3115 cmꢁ1 (NeH str), 2921 cmꢁ1
d
(methyl, CeH str-asym), 2856 cmꢁ1 (CeH str-sym), 1672 cmꢁ1
(amide C]O), 1502 cmꢁ1 (CeN str), 1378 cmꢁ1 (CeNO2), 1644,
1600, 1540, 1500 cmꢁ1 (aromatic ring). 1H NMR (400 MHz, DMSO)
dine), 7.07 (q, J ¼ 8.41, 2H), 7.24 (t, J ¼ 7.21, 1H), 7.33 (q, J ¼ 6.9, 2H),
7.37 (m, 2H), 7.63 (m, 1H), 8.3 (s, 1H, NeH). 13C NMR (100 MHz,
DMSO)
d
15.2, 55.2, 106.4, 115.3 (2), 121.8, 121.9, 124.5, 125.2, 125.9,
d 2.48 (s, 3H, CH3), 4.3 (s, 2H, NeH), 5.39 (s, 1H, Pyrimidine), 7.24
128.6 (2), 138.8, 149.0, 159.1, 160.9, 163.1, 174.5 (2). ESI-MS m/z:
calcd for C19H15FN4OS2 found 398.47 (MþH)þ: 400.06; (Mꢁ1)ꢁ:
396.81.
(m, 1H), 7.33 (dd, J ¼ 7.87, 2H), 7.37 (dd, J ¼ 8.3, 1H), 7.63 (m, 1H),
7.80 (m, 1H), 8.06 (dd, J ¼ 6.7, 2H), 8.9 (s, 1H, NeH). 13C NMR
(100 MHz, DMSO) d 15.2, 57.2, 106.4,121.8, 122.9,124.4, 125.2,125.9,
129.2 (2), 131.3, 131.5, 140.2, 149.0, 159.1, 163.1, 174.5 (2). ESI-MS m/
z: calcd for C19H15N5O3S2 found 425.48 (MþH)þ: 427.05; (Mꢁ1)ꢁ:
423.52.
4.1.2.6. N-(benzo[d]thiazol-2-yl)-4-(4-(trifluoromethyl)phenyl)-
1,2,3,4-tetrahydro-6-methyl-2-thioxopyrimidine-5-carboxamide (7f).
Yield: 68%. m.p. 239e241 ꢀC. IR (KBr)
n
¼ 3118 cmꢁ1 (NeH str),
2927 cmꢁ1 (methyl, CeH str-asym), 2854 cmꢁ1 (CeH str-sym),
1674 cmꢁ1 (amide C]O), 1501 cmꢁ1 (CeN str), 1155 cmꢁ1 (CeF),
1645, 1600, 1540, 1501 cmꢁ1 (aromatic ring). 1H NMR (400 MHz,
4.1.2.11. N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydro-4-(2-
methoxyphenyl)-6-methyl-2-thioxopyrimidine-5-carboxamide (7k).
Yield: 67%. m.p. 256e258 ꢀC. IR (KBr)
n
¼ 3123 cmꢁ1 (NeH str),
DMSO)
d
2.51 (s, 3H, CH3), 4.1 (s, 2H, NeH), 5.31 (s, 1H, Pyrimidine),
2926 cmꢁ1 (methyl, CeH str-asym), 2853 cmꢁ1 (CeH str-sym),
1671 cmꢁ1 (amide C]O), 1505 cmꢁ1 (CeN str), 1402 cmꢁ1
(CH3eOeC), 1644, 1600, 1540, 1500 cmꢁ1 (aromatic ring). 1H NMR
7.24 (m, 2H), 7.37 (t, J ¼ 8.53, 1H), 7.63 (m, 2H), 7.65 (s, 2H), 7.82 (dd,
J ¼ 6.7, 1H), 8.6 (s, 1H, NeH). 13C NMR (100 MHz, DMSO)
d 15.4, 55.1,
106.4, 121.6, 121.9, 124.3, 124.5, 125.0 (2), 125.2, 125.9, 127.3 (2),
(400 MHz, DMSO) d 2.1 (s, 3H, CH3), 3.81 (s, 3H, OCH3), 4.2 (s, 2H,
129.4, 146.5, 149.1, 159.2, 163.1, 174.5 (2). ESI-MS m/z: calcd for
C
NeH), 5.37 (s, 1H, Pyrimidine), 6.94 (t, J ¼ 7.46, 1H), 7.04 (m, 1H),
20H15F3N4OS2 found 448.48 (MþH)þ: 450.03; (Mꢁ1)ꢁ: 446.94.
7.23 (m, 2H), 7.37 (m, 1H), 7.63 (m, 1H), 7.8 (m, 2H), 8.7 (s, 1H, NeH).
13C NMR (100 MHz, DMSO)
d 15.8, 45.3, 56.2, 106.4, 114.1, 120.9,
4.1.2.7. N-(benzo[d]thiazol-2-yl)-4-(4-bromophenyl)-1,2,3,4-
121.4, 121.8, 121.9, 124.5, 125.4,125.9,127.8, 128.1, 149.0, 156.6, 159.1,
163.1, 174.5 (2). ESI-MS m/z: calcd for C20H18N4O2S2 found 410.51
(MþH)þ: 412.02; (Mꢁ1)ꢁ: 409.01.
tetrahydro-6-methyl-2-thioxopyrimidine-5-carboxamide
(7g).
Yield: 59%. m.p. 267e269 ꢀC. IR(KBr)
n
¼ 3118 cmꢁ1 (NeH str),
2923 cmꢁ1 (methyl, CeH str-asym), 2855 cmꢁ1 (CeH str-sym),
1675 cmꢁ1 (amide C]O), 1505 cmꢁ1 (CeN str), 450 cmꢁ1 (CeBr)
1644, 1600, 1540, 1500 cmꢁ1 (aromatic ring). 1H NMR (400 MHz,
4.1.2.12. N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydro-4-(4-
methoxyphenyl)-6-methyl-2-thioxopyrimidine-5-carboxamide (7l).
DMSO)
7.24 (m,1H), 7.28 (m, 2H), 7.33 (m, 2H), 7.37 (m,1H), 7.63 (q, J ¼ 7.01,
1H), 7.8 (m, 1H), 8.6 (s, 1H, NeH). 13C NMR (100 MHz, DMSO)
15.8,
d
2.50 (s, 3H, CH3), 4.1 (s, 2H, NeH), 5.32 (s, 1H, Pyrimidine),
Yield: 77ꢁ%1. m.p. 226e228 ꢀC. IR (KBr)
n
¼ 3116 cmꢁ1 (NeH str),
2926 cm
(methyl, CeH str-asym), 2853 cmꢁ1 (CeH str-sym),
d
1671 cmꢁ1 (amide C]O), 1505 cmꢁ1 (CeN str), 1402 cmꢁ1
55.3, 106.4, 121.8, 121.9, 124.4, 125.2, 125.9, 129.2 (2), 131.3, 131.5,
(CH3eOeC), 1644, 1600, 1540, 1500 cmꢁ1 (aromatic ring). 1H NMR
140.2, 149.0, 159.1, 163.1, 174.5 (2). ESI-MS m/z: calcd for
C
(400 MHz, DMSO) d 1.26 (s, 3H, CH3), 2.37 (s, 3H, OCH3), 4.09 (s, 2H,
19H15BrN4OS2 found 459.38 (MþH)þ: 461.01; (Mꢁ1)ꢁ: 457.98.
NeH), 6.65 (s, 1H, Pyrimidine), 7.18 (q, J ¼ 8.44, 2H), 7.24 (m, 1H),
7.28 (t, J ¼ 7.1, 1H), 8.02 (t, J ¼ 7.1, 1H), 8.17 (q, J ¼ 8.37, 2H), 8.33 (m,
4.1.2.8. N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydro-6-methyl-4-(2-
1H), 8.34 (m, 1H). 13C NMR (100 MHz, DMSO)
d 15.8, 45.3, 56.2,
nitrophenyl)-2-thioxopyrimidine-5-carboxamide (7h). Yield: 66ꢁ%1.
(methyl, CeH str-asym), 2851 cmꢁ1 (CeH str-sym), 1672 cmꢁ1
(amide C]O), 1502 cmꢁ1 (CeN str), 1375 cmꢁ1 (CeNO2), 1644,
1600, 1540, 1500 cmꢁ1 (aromatic ring). 1H NMR (400 MHz, DMSO)
106.4,114.1,120.9,121.3,121.8,121.9,124.5,125.0,125.3,127.8,128.0,
m.p. 231e233 ꢀC. IR (KBr)
n
¼ 3119 cmꢁ1 (NeH str), 2922 cm
149.1, 156.8, 159.1, 163.5, 174.5 (2). ESI-HRMS m/z: calcd for
C
20H18N4O2S2 found 410.01 (MþH)þ: 412.12; (Mꢁ1)ꢁ: 410.01.
4.1.2.13. N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydro-4-(2-
d
2.52 (s, 3H, CH3), 4.3 (s, 2H, NeH), 5.39 (s, 1H, Pyrimidine), 7.24 (t,
hydroxyphenyl)-6-methyl-2-thioxopyrimidine-5-carboxamide (7m).
J ¼ 8.53, 1H), 7.37 (t, J ¼ 7.39, 1H), 7.45 (m, 1H), 7.54 (t, J ¼ 7.9, 1H),
Yield: 68%. m.p. 234e236 ꢀC. IR (KBr)
n
¼ 3132 cmꢁ1 (NeH str),
7.63 (dd, J ¼ 7.5, 1H), 7.71 (t, J ¼ 8.53, 1H), 7.8 (d, J ¼ 8.1, 1H), 8.07 (m,
2922 cmꢁ1 (methyl, CeH str-asym), 2916.12 cmꢁ1 (OeH),
2855 cmꢁ1 (CeH str-sym), 1669 cmꢁ1 (amide C]O), 1501 cmꢁ1
(CeN str), 1644, 1600, 1540, 1500 cmꢁ1 (aromatic ring). 1H NMR
1H), 8.9 (s, 1H, NeH). 13C NMR (100 MHz, DMSO)
d 15.2, 55.2, 106.4,
121.8, 121.9, 124.4, 125.2, 125.9, 129.2 (2), 131.3, 131.5, 140.2, 149.0,
159.1, 163.1, 174.5 (2). ESI-MS m/z: calcd for C19H15N5O3S2 found
425.48 (MþH)þ: 427.05; (Mꢁ1)ꢁ: 423.52.
(400 MHz, DMSO)
d 1.26 (s, 3H, CH3), 4.3 (s, 2H, NeH), 5.33 (s, 1H,
Pyrimidine), 6.67 (m,1H), 6.94 (t, J ¼ 8.29,1H), 7.24 (m,1H), 7.37 (m,
2H), 7.38 (m, 1H), 7.63 (dd, J ¼ 7.3, 1H), 7.8 (m, 1H), 8.5 (s, 1H, NeH),
4.1.2.9. N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydro-6-methyl-4-(3-
10.1 (s, 1H, OeH). 13C NMR (100 MHz, DMSO)
d 15.2, 45.0, 106.4,
nitrophenyl)-2-thioxopyrimidine-5-carboxamide (7i). Yield: 84ꢁ%1.
(methyl, CeH str-asym), 2851 cmꢁ1 (CeH str-sym), 1672 cmꢁ1
(amide C]O), 1502 cmꢁ1 (CeN str), 1375 cmꢁ1 (CeNO2), 1644,
1600, 1540, 1500 cmꢁ1 (aromatic ring). 1H NMR (400 MHz, DMSO)
115.7, 121.2, 121.8, 121.9, 122.9, 124.5, 125.2, 125.9, 128.2, 128.4,
m.p. 244e246 ꢀC. IR (KBr)
n
¼ 3120 cmꢁ1 (NeH str), 2924 cm
149.0, 154.1, 159.1, 163.1, 175.5 (2). ESI-MS m/z: calcd for
C
19H16N4O2S2 found 396.48 (MþH)þ: 397.07; (Mꢁ1)ꢁ: 396.40.
4.1.2.14. N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydro-4-(4-
d
2.49 (s, 3H, CH3), 4.3 (s, 2H, NeH), 5.46 (s, 1H, Pyrimidine), 7.24 (t,
hydroxyphenyl)-6-methyl-2-thioxopyrimidine-5-carboxamide (7n).
J ¼ 8.5, 1H), 7.37 (t, J ¼ 7.85, 1H), 7.44 (t, J ¼ 8.7, 1H), 7.63 (dd, J ¼ 8.2,
Yield: 70%. m.p. 221e224 ꢀC. IR (KBr)
n
¼ 3129 cmꢁ1 (NeH str),
1H), 7.8 (dd, J ¼ 8.4, 1H), 7.87 (m, 1H), 8.03 (t, J ¼ 7.87, 1H), 8.20 (m,
2922 cmꢁ1 (methyl, CeH str-asym), 2916.12 cmꢁ1 (OeH),
2855 cmꢁ1 (CeH str-sym), 1669 cmꢁ1 (amide C]O), 1501 cmꢁ1
(CeN str), 1644, 1600, 1540, 1500 cmꢁ1 (aromatic ring). 1H NMR
1H), 8.9 (s, 1H, NeH). 13C NMR (100 MHz, DMSO)
d 15.2, 55.2, 106.4,
121.8, 121.9, 124.4, 125.2, 125.9, 129.2 (2), 131.3, 131.5, 140.2, 149.0,
159.1, 163.1, 174.5 (2). ESI-HRMS m/z: calcd for C19H15N5O3S2 found
425.48 (MþH)þ: 427.05; (Mꢁ1)ꢁ: 423.52.
(400 MHz, DMSO)
d 2.14 (s, 3H, CH3), 4.30 (s, 2H, NeH), 5.33 (s, 1H,
Pyrimidine), 6.67 (m,1H), 6.94 (t, J ¼ 8.29,1H), 7.24 (m,1H), 7.37 (m,
2H), 7.38 (m, 1H), 7.63 (dd, J ¼ 7.3, 1H), 7.8 (m, 1H), 8.5 (s, 1H, NeH),
4.1.2.10. N-(benzo[d]thiazol-2-yl)-1,2,3,4-tetrahydro-6-methyl-4-(4-
10.1 (s, 1H, OeH). 13C NMR (100 MHz, DMSO)
d 15.7, 45.2, 106.4,
nitrophenyl)-2-thioxopyrimidine-5-carboxamide (7j). Yield: 68%.
115.8, 121.2, 121.8, 121.9, 122.9, 124.5, 125.2, 125.9, 128.2 (2), 149.0,