Molecules 2018, 23, 59
10 of 17
2-(2-(2-((5-((4-(trifluoromethyl◦)phenyl)amino)-1,3,4-thiadiazol-2-yl)thio)acetamido)thiazol-4-yl)acetate (
(cm−1): 3246.20, 3196.05 (N-H stretching), 3140.11 (Aromatic
max
3).
Yield: 87%. m.p.: 222.3–224.1 C. IR
ν
C-H stretching), 2922.16, 2848.86, 2719.63 (Aliphatic C-H stretching), 1716.65 (C=O stretching), 1685.79
(C=O stretching), 1618.28, 1560.41, 1521.84, 1498.69 (N-H bending, C=N and C=C stretching), 1413.82,
1367.53 (C-H bending), 1317.38, 1259.52, 1207.44, 1161.15, 1114.86, 1066.64, 1058.92, 1028.06 (C-N, C-O
stretching and aromatic C-H in plane bending), 958.62, 937.40, 877.61, 840.96, 792.74, 744.52, 729.09,
1
682.80, 632.65 (Aromatic C-H out of plane bending and C-S stretching). H NMR (400 MHz, DMSO-d6)
δ
(ppm): 1.18 (t, J = 6.8 Hz, 7.2 Hz, 3H), 3.69 (s, 2H), 4.08 (q, J = 6.8 Hz, 2H), 4.21 (s, 2H), 7.01 (s, 1H),
7.68 (d, J = 9.2 Hz, 2H), 7.76 (d, J = 8.8 Hz, 2H), 10.79 (brs, 1H), 12.48 (brs, 1H). 13C NMR (100 MHz,
DMSO-d6): 14.07 (CH3), 36.61 (CH2), 36.85 (CH2), 60.31 (CH2), 110.72 (CH), 117.19 (2CH), 121.70 (d, J =
32.1 Hz, C), 125.92 (C), 126.42 (d, J = 3.2 Hz, 2CH), 143.50 (C), 153.39 (C), 157.49 (C), 164.35 (C), 166.02
(C), 169.98 (2C). HRMS (ESI) (m/z): [M + H]+ calcd. for C18H16F3N5O3S3: 504.0440, found: 504.0445.
N-(Benzothiazol-2-yl)-2-((5-((4-(trifluoromethyl)phenyl)amino)-1,3,4-thiadiazol-2-yl)thio)acetamide (
4). Yield:
◦
85%. m.p.: 293.8–294.5 C. IR
ν
max
(cm−1): 3232.70, 3182.55 (N-H stretching), 3138.18, 3066.82, 3037.89
(Aromatic C-H stretching), 2953.02, 2916.37, 2831.50, 2729.27 (Aliphatic C-H stretching), 1681.93 (C=O
stretching), 1602.85, 1566.20, 1444.68 (N-H bending, C=N and C=C stretching), 1417.68, 1382.96 (C-H
bending), 1323.17, 1267.23, 1232.51, 1163.08, 1109.07, 1068.56, 1047.35, 1012.63 (C-N stretching and
aromatic C-H in plane bending), 983.70, 873.75, 846.75, 833.25, 802.39, 756.10, 727.16, 678.94, 657.73
1
(Aromatic C-H out of plane bending and C-S stretching). H NMR (400 MHz, DMSO-d6)
δ (ppm):
4.32 (s, 2H), 7.32 (t, J = 7.6 Hz, 1H), 7.45 (t, J = 7.6 Hz, 1H), 7.67 (d, J = 8.8 Hz, 2H), 7.74–7.78 (m,
3H), 7.98 (d, J = 7.6 Hz, 1H), 10.79 (brs, 1H), 12.68 (brs, 1H). 13C NMR (100 MHz, DMSO-d6): 37.03
(CH2), 117.17 (2CH), 120.63 (CH), 121.71 (d, J = 32.1 Hz, C), 121.75 (CH), 123.68 (CH), 125.81 (CH),
126.18 (C), 126.41 (d, J = 3.9 Hz, 2CH), 131.44 (C), 143.46 (C), 148.48 (C), 153.30 (C), 157.77 (C), 164.38
(C), 167.10 (C). HRMS (ESI) (m/z): [M + H]+ calcd. for C18H12F3N5OS3: 468.0229, found: 468.0213.
N-(6-Fluorobenzothiazol-2-yl)-2-((5-((4-(trifluoromethyl)phenyl)amino)-1,3,4-thiadiazol-2-yl)thio)acetamide
◦
(5
). Yield: 87%. m.p.: 309.9–310.8 C. IR
ν
(cm−1): 3238.48, 3186.40 (N-H stretching), 3082.25
max
(Aromatic C-H stretching), 2951.09, 2916.37, 2854.65, 2792.93, 2723.49 (Aliphatic C-H stretching),
1678.07 (C=O stretching), 1608.63, 1589.34, 1566.20, 1450.47 (N-H bending, C=N and C=C stretching),
1419.61, 1382.96 (C-H bending), 1327.03, 1249.87, 1168.86, 1112.93, 1068.56, 1051.20, 1012.63 (C-N
stretching and aromatic C-H in plane bending), 983.70, 918.12, 873.75, 835.18, 817.82, 804.32,
748.38, 707.88, 673.16, 659.66 (Aromatic C-H out of plane bending and C-S stretching). 1H NMR
(400 MHz, DMSO-d6)
δ (ppm): 4.31 (s, 2H), 7.30 (td, J = 2.8 Hz, 1H), 7.67 (d, J = 8.4 Hz, 2H),
7.74–7.79 (m, 3H), 7.90 (dd, J = 2.4, 8.8 Hz, 1H), 10.79 (s, 1H), 12.70 (brs, 1H). 13C NMR (100 MHz,
DMSO-d6): 36.99 (CH2), 108.21 (d, J = 26.9 Hz, CH), 114.31 (d, J = 24.4 Hz, CH), 117.17 (2CH),
121.72 (d, J = 32.1 Hz, C), 121.77 (d, J = 9.6 Hz, CH), 125.82 (C), 126.41 (d, J = 3.8 Hz, 2CH),
132.70 (d, J = 10.9 Hz, C), 143.47 (C), 145.22 (C), 153.27 (C), 157.50 (C), 159.88 (C), 164.39 (C),
167.22 (C). HRMS (ESI) (m/z): [M + H]+ calcd. for C18H11F4N5OS3: 486.0135, found: 486.0131.
N-(6-Chlorobenzothiazol-2-yl)-2-((5-((4-(trifluoromethyl)phenyl)amino)-1,3,4-thiadiazol-2-yl)thio)acetamide
◦
(6
). Yield: 90%. m.p.: 317.3–318.1 C. IR
ν
(cm−1): 3232.70, 3180.62 (N-H stretching), 3136.25,
max
3072.60, 3035.96 (Aromatic C-H stretching), 2951.09, 2914.44, 2825.72, 2713.84 (Aliphatic C-H
stretching), 1678.07 (C=O stretching), 1602.85, 1566.20, 1448.54 (N-H bending, C=N and C=C
stretching), 1417.68, 1382.96 (C-H bending), 1325.10, 1265.30, 1236.37, 1165.00, 1111.00, 1099.43,
1068.56, 1051.20, 1012.63 (C-N stretching and aromatic C-H in plane bending), 981.77, 879.54,
846.75, 817.82, 806.25, 765.74, 746.45, 692.44, 659.66 (Aromatic C-H out of plane bending and
C-S stretching). 1H NMR (400 MHz, DMSO-d6)
δ (ppm): 4.32 (s, 2H), 7.47 (d, J = 8.8 Hz, 1H),
7.66–7.77 (m, 5H), 8.14 (s, 1H), 10.80 (s, 1H), 12.79 (brs, 1H). 13C NMR (100 MHz, DMSO-d6):
37.01 (CH2), 117.17 (2CH), 121.48 (CH), 121.56 (C), 121.85 (CH), 126.41 (d, J = 3.8 Hz, 2CH),
126.54 (C), 127.72 (CH), 129.02 (C), 133.16 (C), 143.46 (C), 147.39 (C), 153.26 (C), 158.70 (C), 164.39
(C), 167.36 (C). HRMS (ESI) (m/z): [M + H]+ calcd. for C18H11ClF3N5OS3: 501.9839, found: