J. Zhang et al.
3
-(Benzo[d]thiazol-2-yl)-N-[4-(methylsulfonyl)benzyl]aniline
126.8, 126.5, 125.4, 123.5, 123.4, 122.6, 122.1, 121.8,
?
118.4 ppm; ESI-MS: m/z = 332.1 ([M?H] ).
(
2m, C H N O S ) White solid in 55.2% yield; HPLC
21 18 2 2 2
1
purity: 98.26%; t = 5.17 min; m.p.: 133.2–135.1 °C; H
NMR (600 MHz, CDCl ): d = 8.05 (d, J = 8.1 Hz, 1H),
R
N-[3-(Benzo[d]thiazol-2-yl)phenyl]nicotinamide (2q, C19
H N OS) White solid in 51.7% yield; HPLC purity:
3
1
3 3
7
.92 (d, J = 8.3 Hz, 2H), 7.89 (d, J = 8.0 Hz, 1H), 7.59 (d,
1
9
7.92%; t = 5.86 min; m.p.: 200.0–200.5 °C; H NMR
R
J = 8.3 Hz, 2H), 7.48 (dd, J = 8.1, 7.2 Hz, 1H), 7.38 (dd,
J = 8.0, 7.2 Hz, 1H), 7.43–7.39 (m, 1H), 7.27 (dd, J = 7.8,
(
(
600 MHz, DMSO-d ): d = 10.76 (brs, 1H, NH), 8.84–8.81
m, 2H), 8.66 (dd, J = 1.8, 1.7 Hz, 1H), 8.17 (d,
6
7
4
.2 Hz, 1H), 6.68 (dd, J = 7.9, 1.8 Hz, 1H), 4.55 (brs, 2H),
1
J = 7.6 Hz, 1H), 8.09 (d, J = 8.0 Hz, 1H), 8.02 (dd,
J = 8.1, 1.2 Hz, 1H), 7.94–7.92 (m, 2H), 7.88–7.84 (m,
3
.45 (brs, 1H, NH), 3.05 (s, 3H) ppm;
C NMR
(
150 MHz, CDCl ): d = 168.5, 154.1, 148.0, 146.0, 139.6,
3
1
7
H), 7.59 (dd, J = 8.0, 7.9 Hz, 1H), 7.57 (dd, J = 7.6,
1
35.1, 134.7, 130.2, 128.1, 128.0, 126.4, 125.3, 123.3,
1
.1 Hz, 1H), 7.49 (dd, J = 8.0, 7.1 Hz, 1H) ppm; C NMR
3
1
21.7, 117.8, 115.4, 111.5, 47.7, 44.7 ppm; ESI-MS: m/
(
150 MHz, DMSO-d ): d = 167.1, 164.3, 153.5, 150.3,
?
z = 395.0 ([M?H] ).
6
141.6, 139.6, 134.5, 133.3, 129.9, 126.8, 125.7, 123.0,
3
-(Benzo[d]thiazol-2-yl)-N-(naphthalen-2-ylmethyl)aniline
122.9, 122.5, 121.6, 118.6 ppm; ESI-MS: m/z = 332.0
?
([M?H] ).
(
2n, C H N S) Yellow oil in 56.1% yield; HPLC purity:
2
4 18 2
1
9
6.10%; t = 12.19 min; H NMR (600 MHz, DMSO-d ):
R 6
N-[3-(Benzo[d]thiazol-2-yl)phenyl]isonicotinamide (2r, C19
H N OS) White solid in 62.3% yield; HPLC purity:
d = 8.10 (d, J = 7.6 Hz, 1H), 8.01 (d, J = 7.9 Hz, 1H),
.93–7.85 (m, 4H), 7.57 (dd, J = 8.5, 1.5 Hz, 1H), 7.52
dd, J = 7.6, 7.0 Hz, 1H), 7.50–7.45 (m, 2H), 7.43 (dd,
J = 7.9, 7.0 Hz, 1H), 7.41 (brs, 1H), 7.25–7.20 (m, 2H),
1
3 3
7
1
9
8.13%; t = 5.58 min; m.p.: 221.7–222.5 °C; H NMR
R
(
(
600 MHz, DMSO-d ): d = 10.71 (brs, 1H, NH), 9.17 (d,
6
J = 1.7 Hz, 1H), 8.79 (dd, J = 4.8, 1.7 Hz, 1H), 8.66 (brs,
1
3
6
.83–6.78 (m, 2H), 4.54 (d, J = 6.0 Hz, 2H) ppm;
C
1H), 8.38–8.34 (m, 1H), 8.17 (d, J = 7.9 Hz, 1H), 8.09 (d,
NMR (150 MHz, DMSO-d ): d = 168.2, 153.5, 149.3,
6
J = 8.0 Hz, 1H), 8.02 (d, J = 8.1 Hz, 1H), 7.85 (d,
J = 7.9 Hz, 1H), 7.62–7.55 (m, 3H), 7.48 (dd, J = 8.0,
1
1
1
37.5, 134.3, 133.4, 133.0, 132.2, 129.9, 128.0, 127.6,
27.5, 126.5, 126.2, 125.9, 125.6, 125.3, 125.3, 122.7,
1
3
7
.1 Hz, 1H) ppm; C NMR (150 MHz, DMSO-d6):
d = 167.1, 164.4, 153.5, 152.3, 148.8, 139.8, 135.5, 134.5,
33.3, 130.3, 129.9, 126.7, 125.6, 123.5, 122.9, 122.9,
22.3, 115.1, 114.9, 110.6, 46.6 ppm; ESI-MS: m/
?
z = 367.0 ([M?H] ).
1
?
3
-(Benzo[d]thiazol-2-yl)-N-(naphthalen-1-ylmethyl)aniline
122.7, 122.5, 118.5 ppm; ESI-MS: m/z = 332.1 ([M?H] ).
(
9
2o, C H N S) White solid in 50.7% yield; HPLC purity:
24 18 2
N-[3-(Benzo[d]thiazol-2-yl)phenyl]quinoline-2-carboxamide
1
6.96%; t = 12.64 min; m.p.: 103.0–105.4 °C; H NMR
R
(
2s, C H N OS) White solid in 82.5% yield; HPLC
23 15 3
1
(
(
600 MHz, DMSO-d ): d = 8.19 (d, J = 8.3 Hz, 1H), 8.10
6
purity: 96.22%; t = 11.40 min; m.p.: 194.2–196.1 °C; H
R
d, J = 7.7 Hz, 1H), 8.01 (d, J = 8.0 Hz, 1H), 7.97 (d,
NMR (600 MHz, CDCl ): d = 10.44 (brs, 1H, NH), 8.48
3
J = 7.3 Hz, 1H), 7.85 (d, J = 8.1 Hz, 1H), 7.60 (dd,
J = 8.0, 7.8 Hz, 1H), 7.58–7.55 (m, 2H), 7.51 (dd, J = 8.1,
(brs, 1H), 8.42 (d, J = 8.8 Hz, 1H), 8.39 (d, J = 8.4 Hz,
1
7
7
H), 8.27–8.21 (m, 2H), 8.11 (d, J = 8.0 Hz, 1H),
.96–7.90 (m, 2H), 7.88–7.81 (m, 2H), 7.67 (dd, J = 8.4,
.8 Hz, 1H), 7.56 (dd, J = 8.8, 7.8 Hz, 1H), 7.52 (dd,
7
.8 Hz, 1H), 7.48 (dd, J = 8.3, 7.2 Hz, 1H), 7.43 (dd,
J = 7.9, 7.3 Hz, 1H), 7.42 (brs, 1H), 7.27–7.23 (m, 2H),
.86–6.81 (m, 1H), 6.69 (t, J = 5.6 Hz, 1H, NH), 4.81 (d,
6
J = 7.6, 7.4 Hz, 1H), 7.41 (dd, J = 7.4, 7.4 Hz, 1H) ppm;
13
1
3
J = 5.6 Hz, 2H) ppm; C NMR (150 MHz, DMSO-d6):
C NMR (150 MHz, CDCl ): d = 167.8, 162.6, 154.2,
3
d = 168.2, 153.5, 149.5, 134.6, 134.3, 133.5, 133.4, 131.1,
1
1
1
1
1
49.5, 146.5, 138.8, 138.1, 135.3, 134.5, 130.6, 130.1,
29.9, 128.5, 127.5, 126.5, 126.2, 125.8, 125.5, 125.3,
29.9, 129.7, 128.4, 128.0, 126.6, 125.5, 123.6, 123.4,
25.1, 123.7, 122.7, 122.3, 115.0, 114.9, 110.2, 44.5 ppm;
?
22.2, 121.8, 118.8, 118.3 ppm; ESI-MS: m/z = 382.1
?
ESI-MS: m/z = 367.0 ([M ?H] ).
([M?H] ).
N-[3-(Benzo[d]thiazol-2-yl)phenyl]picolinamide (2p, C19
H N OS) White solid in 69.0% yield; HPLC purity:
N-[3-(Benzo[d]thiazol-2-yl)phenyl]-2-(1H-indol-3-yl)acetamide
2t, C H N OS) White solid in 63.2% yield; HPLC pur-
13 3
(
1
22 15 3
9
8.41%; t = 7.41 min; m.p.: 177.7–178.9 °C; H NMR
R
1
ity: 97.81%; t = 6.02 min; m.p.: 218.1–219.5 °C;
H
R
(
600 MHz, CDCl ): d = 10.23 (brs, 1H, NH), 8.65 (d,
3
NMR (600 MHz, DMSO-d ): d = 10.95 (brs, 1H, NH),
6
J = 4.3 Hz, 1H), 8.45 (dd, J = 1.7, 1.8 Hz, 1H), 8.33 (d,
J = 7.6 Hz, 1H), 8.11 (dd, J = 8.1, 1.8 Hz, 1H), 8.09 (d,
J = 8.1 Hz, 1H), 7.96–7.91 (m, 2H), 7.86 (d, J = 7.7 Hz,
10.40 (brs, 1H, NH), 8.51 (dd, J = 1.8, 1.7 Hz, 1H), 8.14
(d, J = 7.9 Hz, 1H), 8.06 (d, J = 8.1 Hz, 1H), 7.79 (d,
J = 8.1 Hz, 1H), 7.74 (d, J = 7.7 Hz, 1H), 7.64 (d,
J = 8.0 Hz, 1H), 7.55 (dd, J = 7.9, 7.0 Hz, 1H), 7.49 (dd,
J = 8.4, 8.0 Hz, 1H), 7.47 (dd, J = 8.1, 7.0 Hz, 1H), 7.37
1
H), 7.55–7.49 (m, 3H), 7.40 (dd, J = 7.7, 7.1 Hz, 1H)
1
3
ppm; C NMR (150 MHz, CDCl ): d = 167.8, 162.4,
3
1
54.2, 149.7, 148.2, 138.7, 137.9, 135.3, 134.5, 130.1,
(d, J = 8.4 Hz, 1H), 7.30 (d, J = 2.4 Hz, 1H), 7.08 (dd,
1
23