6
WU ET AL.
7.31 (s, 2H, Ph H), 7.07 (d, 2H, J = 8.4 Hz, Ph H), 4.30
(s, 2H, SCH2 ), 3.82 (s, 6H, CH3O ), 3.70(s, 3H,
CH3O ), 3.68-3.61 (m, 4H), 3.39-3.28 (m, 4H); 13C NMR
(DMSO-d6, 125 MHz) δ: 170.69, 166.43, 153.67, 153.34,
143.38, 139.20, 128.05 (q, J = 268.5 Hz), 126.71, 118.86 (q,
J = 31.6 Hz), 111.01, 103.75, 60.50 56.42, 47.52, 47.17,
45.39, 41.61, 35.24; MS (ESI) m/z: 538.1([M + H]+); Anal.
calcd for C24H26F3N5O4S: C 53.62, H 4.88, N 13.03; found:
C 53.65, H 4.91, N 13.00.
(s, 6H, CH3O ), 3.74-3.69 (m, 7H), 3.66-3.56 (m, 4H); 13
C
NMR (DMSO-d6, 125 MHz) δ: 170.71, 166.64, 161.43,
158.41, 155.69, 153.76, 139.57, 122.49, 110.95, 103.93,
60.60, 56.48, 45.64, 43.84, 43.49, 41.87, 34.91; MS (ESI) m/
z: 472.1([M + H]+); Anal. calcd for C21H25N7O4S: C
53.49, H 5.34, N 20.79; found: C 53.51, H 5.35, N 20.82.
4.4.13 | 1-(4-Benzylpiperazin-1-yl)-
2-((5-[3,4,5-trimethoxyphenyl]-4H-
1,2,4-triazol-3-yl)thio)ethanone (6m)
4.4.10 | 1-(4-[Pyridin-2-yl]piperazin-1-yl)-
2-((5-[3,4,5-trimethoxyphenyl]-4H-1,2,4-
triazol-3-yl)thio)ethanone (6j)
White solid; yield 58.2%; mp 159-160ꢀС; (500 MHz,
DMSO-d6) δ: 14.38 (s, 1H, N H), 7.29 (s, 2H, Ph H),
7.23 (t, 2H, J = 5.0 Hz, Ph H), 6.95(d, 2H, J = 7.0 Hz,
Ph H), 6.82 (t, 1H, J = 6.0 Hz, Ph H), 4.39 (s, 2H,
CH2 ), 4.28 (s, 2H, CH2 ), 3.84 (s, 6H, CH3O ), 3.72 (s,
3H, CH3O ), 3.62-3.58 (m, 4H), 3.19-3.11 (m, 4H); 13C
NMR (DMSO-d6, 125 MHz) δ: 170.75, 166.43, 159.57,
155.65, 153.61, 139.17, 129.74, 119.83, 116.52, 103.83,
60.59, 56.48, 48.70, 41.94; MS (ESI) m/z: 484.0 ([M
+ Na]+); Anal. calcd for C24H29N5O4S: C 59.61, H 6.04, N
14.48; found: C 59.62, H 6.07, N 14.47.
White solid; yield 41.8%; mp 164-166ꢀС; 1H NMR
(500 MHz, DMSO-d6) δ: 14.37 (s, 1H, N H), 8.14(d, 1H,
J = 5.0 Hz, pyridine H), 7.56 (t, 1H, J = 7.0 Hz,
Pyridine H), 7.28 (s, 2H, Ph H), 6.86 (d, 1H, J = 7.0 Hz,
Pyridine H), 6.68 (t, 1H, J = 5.0 Hz, Ph H), 4.25 (s, 2H,
SCH2 ), 3.84 (s, 6H, CH3O ), 3.71 (s, 3H, CH3O ),
3.68-3.59 (m, 8H); 13C NMR (DMSO-d6, 125 MHz) δ:
170.71, 166.40, 159.57, 155.64, 153.62, 148.05, 138.36,
122.32, 113.96, 107.63, 103.83, 60.60, 56.26, 44.83, 41.75,
34.67; MS (ESI) m/z: 493.0([M + Na]+); Anal. calcd for
C22H26N6O4S: C 56.16, H 5.57, N 17.86; found: C 56.17, H
5.54, N 17.85.
4.4.14 | 1-(4-[Furan-2-carbonyl]
piperazin-1-yl)-2-((5-[3,4,5-
trimethoxyphenyl]-4H-1,2,4-triazol-3-yl)
thio)ethanone (6n)
4.4.11 | 1-(4-[Pyridin-4-yl]piperazin-1-yl)-
2-((5-[3,4,5-trimethoxyphenyl]-4H-1,2,4-
triazol-3-yl)thio)ethanone (6k)
Yellow solid; yield 75.6%; mp 195-196ꢀС; 1H NMR
(500 MHz, DMSO-d6) δ: 14.39 (s, 1H, N H), 7.85 (s, 1H,
Furan H), 7.27 (s, 2H, Ph H), 7.03(d, 1H, J = 3.0 Hz,
Furan H), 7.03-7.01 (m, 1H, Furan H), 4.24 (s, 2H,
SCH2 ), 3.84 (s, 6H, CH3O ), 3.70(s, 3H, CH3O ),
3.68-3.61 (m, 4H), 3.57-3.51 (m, 4H); 13C NMR (DMSO-d6,
125 MHz) δ: 170.83, 166.39, 154.22, 153.62, 139.43, 123.93,
103.83, 79.67, 60.83, 56.26, 45.78, 41.79, 35.19, 28.31; MS
(ESI) m/z: 516.1([M + Na]+); Anal. calcd for C22H25N5O6S:
C 54.20, H 5.17, N 14.36; found: C54.21, H 5.15, N 14.38.
White solid; yield 50.6%; mp 151-153ꢀС; 1H NMR
(500 MHz, DMSO-d6) δ: 14.32 (s, 1H, N H), 7.93 (d, 1H,
J = 8.4 Hz, pyridine H), 7.38 (d, 1H, J = 8.4 Hz,
Pyridine H), 7.28 (s, 2H, Ph H), 4.60 (s, 2H, SCH2 ),
3.84 (s, 6H, CH3O ), 3.71 (s, 3H, CH3O ), 3.69-3.58 (m,
8H); 13C NMR (DMSO-d6, 125 MHz) δ: 170.68, 166.39,
153.57, 138.91, 128.21, 127.17, 110.44, 103.82, 103.82,
60.61, 56.25, 44.82, 41.75, 34.53; MS (ESI) m/z: 471.1([M
+ H]+); Anal. calcd for C22H26N6O4S: C 56.16, H 5.57, N
17.86; found: C 56.19, H 5.60, N 17.88.
4.4.15 | Tert-butyl4-(2-((5-[3,4,5-
trimethoxyphenyl]-4H-1,2,4-triazol-3-yl)
thio)acetyl) piperazine-1-carboxylate (6o)
4.4.12 | 1-(4-[Pyrimidin-2-yl]piperazin-
1-yl)-2-((5-[3,4,5-trimethoxyphenyl]-4H-
1,2,4-triazol-3-yl)thio)ethanone (6l)
White solid; yield 61.8%; mp 184-186ꢀС; 1H NMR
(500 MHz, DMSO-d6) δ: 14.30 (s, 1H, N H), 7.27 (s, 2H,
Ph H), 4.24 (s, 2H, SCH2 ), 3.85 (s, 6H, CH3O ), 3.71
(s, 3H, CH3O ), 3.55-3.40 (m, 8H), 1.14 (s, 9H); 13C NMR
(DMSO-d6, 125 MHz) δ: 170.75, 166.42, 158.97, 153.87,
147.27, 145.24, 116.53, 111.94, 103.86, 79.67, 60.60, 56.25,
45.59, 41.97, 35.43; MS (ESI) m/z: 488.1([M + H]+); Anal.
White solid; yield 32.9%; mp 103-105ꢀС; 1H NMR
(500 MHz, DMSO-d6) δ: 14.37 (s, 1H, N H), 8.39 (d, 2H,
J = 4.8 Hz, pyrimidine H), 7.28 (s, 2H, Ph H), 6.67 (t,
1H, J = 4.8 Hz, Pyrimidine H), 4.24 (s, 2H, SCH2 ), 3.84