8
2
P. KUMARI ET AL.
J ¼ 8.4 Hz, 2H, ArH), 7.75 (d, J ¼ 8.4 Hz, 2H, ArH), 7.67 (d, J ¼ 8.4 Hz, 2H, ArH), 7.50
1
3
(
t, J ¼ 7.3 Hz, 2H, ArH), 7.42 (t, J ¼ 7.3 Hz, 1H, ArH), 2.59 (s, 3H, thiazole-CH ).
C
3
NMR (100 MHz, CDCl ): d 168.3 (C ¼ O), 155.6, 154.3, 142.7, 138.1, 136.7, 132.9, 132.1,
3
1
31.9, 128.6, 128.3, 126.9, 122.9, 110.3, 12.2 (CH ). ESI-MS (m/z): 442.12 [M þ H,
3
8
1
þ 79 þ
Br] , 440.11 [M þ H Br] .
Anal. Calcd for C H BrN O S: C, 54.56; H, 3.20. Found: C, 54.49; H, 3.17.
2
0
14
3 2
1
-(5-Methyl-4-phenylthiazol-2-yl)-3-(p-tolyl)-1H-pyrazole-4-carboxylic acid (6c)
ꢀ
ꢂ1
Light pink solid; 75% yield; m.p. 298-299 C. IR (t cm , KBr): 1692 (C ¼ O str), 2559-
1
3
026 (OH str). H NMR (400 MHz, DMSO-d ): d 8.89 (s, 1H, pyrazole-H), 7.76 (d,
6
J ¼ 7.3 Hz, 2H, ArH), 7.71 (d, J ¼ 7.9 Hz, 2H, ArH), 7.50 (t, J ¼ 7.3, Hz, 2H, ArH), 7.41
(
t, J ¼ 7.3 Hz, 1H, ArH), 7.27 (d, J ¼ 7.9 Hz, 2H, ArH), 2.59 (s, 3H, thiazole-CH ), 2.37
3
13
(
1
s, 3H, ArCH ). C NMR (100 MHz, CDCl ): d 169.1 (C ¼ O), 154.5, 148.4, 140.3,
3
3
34.3, 133.2, 129.7, 128.5, 128.4, 128.1, 126.8, 126.8, 110.7, 21.5 (CH ), 12.3 (CH ). ESI-
3 3
þ
MS (m/z): 376.12 [M þ H] .
Anal. Calcd for C H N O S: C, 67.18; H, 4.56. Found: C, 67.11; H, 4.52.
2
1
17 3 2
3
-(4-Methoxyphenyl)-1-(5-methyl-4-phenylthiazol-2-yl)-1H-pyrazole-4-carboxylic
acid (6d)
ꢀ
Light pink solid; 73% yield; m.p. 280-282 C. IR (t cm-1, KBr): 1696 (C ¼ O str), 2565-
1
3
000 (OH str). H NMR (400 MHz, DMSO-d ): d 8.89 (s, 1H, pyrazole-H), 7.75-7.79
6
(
m, 4H, ArH), 7.51 (t, J ¼ 7.2 Hz, 2H, ArH), 7.42 (t, J ¼ 7.3 Hz, 1H, ArH), 7.03 (d,
13
J ¼ 8.8 Hz, 2H, ArH), 3.82 (s, 3H, ArOCH ), 2.59 (s, 3H, thiazole-CH ). C NMR
3
3
(
1
100 MHz, CDCl ): d 169.1 (C ¼ O), 155.1, 148.4, 134.0, 133.1, 128.5, 128.4, 128.1,
3
þ
26.7, 122.2, 114.3, 110.8, 55.1 (OCH ), 12.1 (CH ). ESI-MS (m/z): 392.11 [M þ H] .
3
3
Anal. Calcd for C H N O S: C, 64.43; H, 4.38. Found: C, 64.33; H, 4.34.
2
1
17 3 3
1
-(4-(3-Chlorophenyl)-5-methylthiazol-2-yl)-3-phenyl-1H-pyrazole-4-carboxylic
acid (6e)
ꢀ
ꢂ1
Light pink solid; 87% yield; m.p. 282-284 C. IR (t cm , KBr): 1701 (C ¼ O str), 2574-
1
3
067 (OH str). H NMR (400 MHz, DMSO-d ): d 12.80 (bs, 1H, -OH), 8.99 (s, 1H, pyr-
6
azole-H), 7.84 (t, J ¼ 1.8 Hz, 1H, ArH), 7.79-7.81 (m, 2H, ArH), 7.73 (td, J ¼ 7.6 &
1
.3 Hz, 1H, ArH), 7.53 (t, J ¼ 7.9 Hz, 1H, ArH), 7.45-7.50 (m, 4H, ArH), 2.61 (s, 3H,
13
thiazole-CH ). C NMR (100 MHz, CDCl ): d 169.2 (C ¼ O), 154.5, 146.9, 135.7, 134.5,
3
3
1
33.3, 130.2, 129.8, 129.5, 129.0, 128.5, 128.2, 127.8, 126.9, 126.4, 110.5, 12.8 (CH ).
3
3
7
þ
35
þ
ESI-MS (m/z): 398.13 [M þ H, Cl] , 396.12 [M þ H, Cl] .
Anal. Calcd for C H ClN O S: C, 60.68; H, 3.56. Found: C, 60.61; H, 3.52.
2
0
14
3 2
3
-(4-Bromophenyl)-1-(4-(3-chlorophenyl)-5-methylthiazol-2-yl)-1H-pyrazole-4-
carboxylic acid (6f)
ꢀ
ꢂ1
Light pink solid; 84% yield; m.p. 289-290 C. IR (t cm , KBr): 1699 (C ¼ O str), 2565-
1
3
067 (OH str). H NMR (400 MHz, DMSO-d ): d 9.01 (s, 1H, pyrazole-H), 7.84 (t,
6