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TARIQ ET AL.
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CH2), 7.19–8.44 (m, 12H, Ar-H), 8.87 (s, 1H, NH, D2O exchangeable),
10.83 (s, 1H, NH, D2O exchangeable); 13C NMR (DMSO-d6): δ = 24.17
(CH2), 112.19, 118.38, 120.06, 121.27, 122.64, 125.21, 126.51,
129.96, 130.18, 130.55, 131.04, 132.36, 134.74, 135.92, 138.17,
145.11, 152.28, 161.59, 167.99; ESI-MS (m/z): 468 [M+H]+, 469
[M+2]+; Anal. calcd. for C22H16Cl2N6S: C, 56.54; H, 3.45; N, 17.98.
Found: C, 56.52; H, 3.41; N, 17.93.
[M+H]+, 429 [M+2]+; Anal. calcd. for C16H10Cl3N5OS: C, 45.04;
H, 2.36; N, 16.41. Found: C, 45.02; H, 2.39; N, 16.38.
5-Chloro-N-[3-{(4-chloro-2-methylphenoxy)methyl}-4H-1,2,4-
triazol-4-yl]benzo[d]thiazol-2-amine (4k)
White powder; yield 82%; m.p. 278–280°C; IR: (KBr, cm−1): 2997
(N─H), 1528 (C N), 1221 (Ar-O-C); 1H NMR (300 MHz, DMSO-d6):
δ = 2.15 (s, 3H, CH3), 4.63 (s, 2H, OCH2), 6.85–7.68 (m, 7H, Ar-H),
11.37 (s, 1H, NH, D2O exchangeable); 13C NMR (DMSO-d6): δ = 14.87
(CH3), 69.14 (OCH2), 115.12, 118.63, 121.56, 123.17, 124.59, 128.10,
129.61, 130.11, 131.48, 132.15, 138.47, 139.34, 147.59, 161.12,
168.34; ESI-MS (m/z): 407 [M+H]+, 408 [M+2]+; Anal. calcd. for
N-(3-(1-(4-Isobutylphenyl)ethyl)-4H-1,2,4-triazol-4-yl)benzo[d]-
thiazol-2-amine (4g)
Light yellow powder; yield 77%; m.p. 349–351°C; IR: (KBr, cm−1): 3022
(N─H), 1541 (C N); 1H NMR (300 MHz, DMSO-d6): δ = 0.87 (d, 6H,
J = 2.1 Hz, 2 × CH3), 1.62 (d, 3H, J = 8.4 Hz, CH3), 1.80–1.88 (m, 1H,
CH), 2.46 (d, 2H, J = 5.1 Hz, CH2), 4.08 (q, 1H, J = 7.8 Hz, CH), 7.23–
7.80 (m, 9H, Ar-H), 10.00 (s, 1H, NH, D2O exchangeable); 13C NMR
(DMSO-d6): δ = 20.24 (Ar(CH3)CH-), 22.71 ((CH3)2CHCH2-), 29.51
((CH3)2CHCH2-), 34.73 (Ar(CH3)CH-, 44.61 (CH3)2CHCH2-), 119.53,
123.37, 124.66, 127.13, 127.74, 129.11, 130.18, 131.32, 136.04,
144.46, 151.13, 155.37, 165.41; ESI-MS (m/z): 378 [M+H]+; Anal.
calcd. for C21H23N5S: C, 66.81; H, 6.14; N, 18.55. Found: C, 66.78; H,
6.11; N, 18.56.
C17H13Cl2N5OS: C, 50.26; H, 3.23; N, 17.24. Found: C, 50.23; H, 3.21;
N, 17.27.
5-Chloro-N-[3-(1-phenoxyethyl)-4H-1,2,4-triazol-4-yl]benzo[d]-
thiazol-2-amine (4l)
Light yellow powder; yield 76%; m.p. 307–309°C; IR: (KBr, cm−1): 3017
(N─H), 1521 (C N), 1210 (Ar-O-C); 1H NMR (300 MHz, DMSO-d6):
δ = 1.63 (d, 3H, J = 6.9 Hz, CH3), 4.05 (q, 1H, J = 7.2 Hz, OCH), 6.93–
7.74 (m, 9H, Ar-H), 11.26 (s, 1H, NH, D2O exchangeable); 13C NMR
(DMSO-d6): δ = 19.13 (CH3), 69.04 (OCH), 115.12, 119.13, 122.60,
125.43, 128.11, 129.16, 132.14, 137.79, 138.81, 140.71, 154.19,
155.41, 169.24; ESI-MS (m/z): 373 [M+H]+, 374 [M+2]+; Anal. calcd.
for C17H14ClN5OS: C, 54.91; H, 3.79; N, 18.83. Found: C, 54.88; H,
3.74; N, 18.81.
5-Chloro-N-[3-(phenoxymethyl)-4H-1,2,4-triazol-4-yl]benzo[d]-
thiazol-2-amine (4h)
Light brown powder; yield 77%; m.p. 381–383°C; IR: (KBr, cm−1): 3280
(N─H), 1590 (C N), 1240 (Ar-O-C); 1H NMR (300 MHz, DMSO-d6):
δ = 4.63 (s, 2H, OCH2), 6.95–7.67 (m, 9H, Ar-H), 10.97 (s, 1H, NH,
D2O exchangeable); 13C NMR (DMSO-d6): δ = 68.16 (OCH2), 114.13,
117.85, 119.22, 120.53, 122.24, 123.57, 125.73, 128.92, 129.14,
129.62, 137.25, 151.01, 170.61; ESI-MS (m/z): 359 [M+H]+, 360
[M+2]+; Anal. calcd. for C16H12ClN5OS: C, 53.71; H, 3.38; N, 19.57.
Found: C, 53.67; H, 3.32; N, 19.52.
5-Chloro-N-(3-(2-((2,6-dichlorophenyl)amino)benzyl)-4H-1,2,4-
triazol-4-yl)benzo[d]thiazol-2-amine (4m)
Yellow powder; yield 71%; m.p. 390–392°C; IR: (KBr, cm−1): 3021
(N─H), 1517 (C N); 1H NMR (300 MHz, DMSO-d6): δ = 4.51 (s, 2H,
CH2), 7.13–8.49 (m, 11H, Ar-H), 8.78 (s, 1H, NH, D2O exchangeable),
10.76 (s, 1H, NH, D2O exchangeable); 13C NMR (DMSO-d6): δ = 23.04
(CH2), 113.42, 114.07, 117.38, 121.15, 123.24, 123.62, 125.69,
127.21, 128.52, 129.36, 130.15, 130.71, 131.09, 132.36, 144.21,
148.11, 152.33, 161.59, 167.99; ESI-MS (m/z): 503 [M+H]+, 504
[M+2]+; Anal. calcd. for C22H15Cl3N6S: C, 52.66; H, 3.01; N, 16.75.
Found: C, 52.64; H, 3.03; N, 16.79.
5-Chloro-N-[3-{(4-chlorophenoxy)methyl}-4H-1,2,4-triazol-4-yl]-
benzo[d]thiazol-2-amine (4i)
Light yellow powder; yield 80%; m.p. 317–319°C; IR: (KBr, cm−1): 3311
(N─H), 1567 (C N), 1235 (Ar-O-C); 1H NMR (300 MHz, DMSO-d6):
δ = 4.78 (s, 2H, OCH2), 6.93–7.77 (m, 8H, Ar-H), 10.83 (s, 1H, NH,
D2O exchangeable); 13C NMR (DMSO-d6): δ = 71.18 (OCH2), 114.11,
118.38, 121.25, 124.67, 127.23, 128.51, 129.79, 130.48, 130.15,
132.04, 135.36, 164.45, 170.03; ESI-MS (m/z): 393 [M+H]+, 394
[M+2]+; Anal. calcd. for C16H11Cl2N5OS: C, 48.99; H, 2.83; N, 17.85.
Found: C, 48.92; H, 2.78; N, 17.81.
5-Chloro-N-(3-(1-(4-isobutylphenyl)ethyl)-4H-1,2,4-triazol-4-yl)-
benzo[d]thiazol-2-amine (4n)
Off white powder; yield 70%; m.p. 273–275°C; IR: (KBr, cm−1): 3018
(N─H), 1540 (C N); 1H NMR (300 MHz, DMSO-d6): δ = 0.84 (d, 6H,
J = 7.2 Hz, 2 × CH3), 1.62 (d, 3H, J = 8.4 Hz, CH3), 1.83–1.89 (m, 1H,
CH), 2.51 (d, 2H, J = 5.1 Hz, CH2), 4.10 (q, 1H, J = 4.2 Hz, CH), 7.29–
7.87 (m, 8H, Ar-H), 10.17 (s, 1H, NH, D2O exchangeable); 13C NMR
(DMSO-d6): δ = 19.16 (Ar(CH3)CH─), 22.14 ((CH3)2CHCH2─), 29.59
((CH3)2CHCH2─), 34.81 (Ar(CH3)CH─, 44.81 (CH3)2CHCH2─), 119.49,
123.28, 125.66, 127.23, 127.64, 129.71, 130.13, 130.75, 138.04,
142.36, 151.11, 156.37, 167.11; ESI-MS (m/z): 413 [M+H]+, 414
[M+2]+; Anal. calcd. for C21H22ClN5S: C, 61.23; H, 5.38; N, 17.00.
Found: C, 61.28; H, 5.36; N, 16.97.
5-Chloro-N-[3-{(2,4-dichlorophenoxy)methyl}-4H-1,2,4-triazol-
4-yl]benzo[d]thiazol-2-amine (4j)
Yellow powder; yield 73%; m.p. 293–295°C; IR: (KBr, cm−1): 3311
(N─H), 1568 (C N), 1234 (Ar-O-C); 1H NMR (300 MHz, DMSO-d6):
δ = 4.68 (s, 2H, OCH2), 7.28–7.71 (m, 7H, Ar-H), 11.10 (s, 1H, NH,
D2O exchangeable); 13C NMR (DMSO-d6): δ = 70.13 (OCH2), 114.18,
116.41, 121.84, 124.51, 125.62, 127.80, 129.39, 130.01, 131.95,
132.76, 134.62, 140.23, 144.12, 161.87, 168.93; ESI-MS (m/z): 428