A mixture of 13b and benzoyl chloride in MeCN afforded
A mixture of 13c and benzoyl chloride in MeCN afforded
1
1
1
7
7
4b: H NMR (400 MHz, CDCl
3
) δ 8.07 (1H, s), 7.82 (2H, d, J =
3
14g: H NMR (400 MHz, CDCl ) δ 7.87 (2H, dd, J = 1.6, 7.2
.2 Hz), 7.64 (1H, s), 7.58 (1H, d, J = 8.0 Hz), 7.51 (1H, t, J =
.2 Hz), 7.43 (2H, t, J = 7.2 Hz), 7.35 (1H, d, J = 8.8 Hz), 7.30
Hz), 7.81 (1H, br s), 7.64 (2H, d, J = 8.4 Hz), 7.56 (1H, tt, J =
1.6, 7.2 Hz), 7.50 (2H, t, J = 7.2 Hz), 7.45 (1H, d, J = 8.8 Hz),
7.40 (2H, d, J = 8.4 Hz), 7.14 (1H, d, J = 2.8 Hz), 6.91 (1H, dd,
J = 2.8, 8.8 Hz), 5.37 (1H, br s), 4.61 (2H, s), 4.12 (2H, t, J = 5.6
(
=
(
1H, dd, J = 7.6, 8.0 Hz), 7.12 (1H, d, J = 7.6 Hz), 7.09 (1H, d, J
2.4 Hz), 6.86 (1H, dd, J = 2.4, 8.8 Hz), 6.11 (1H, br s), 4.56
2H, s), 4.08 (2H, t, J = 5.6 Hz), 3.72 (4H, t, J = 4.4 Hz), 2.78
Hz), 3.74 (4H, t, J = 4.8 Hz), 2.80 (2H, t, J = 5.6 Hz), 2.58 (4H, t,
1
3
13
(
2H, t, J = 5.6 Hz), 2.56 (4H, t, J = 4.4 Hz); C NMR (100 MHz,
) δ 154.2, 146.6, 138.8, 138.4, 134.7, 131.9, 131.4, 129.4,
28.7, 127.0, 123.7, 119.6, 119.2, 114.2, 106.5, 66.9, 66.6, 57.7,
4.1, 48.9; HRMS (ESI) m/z calcd for C27 S, 488.1882;
J = 4.8 Hz); C NMR (100 MHz, CD
3
OD + CDCl
3
) δ 188.7,
CDCl
1
5
3
166.6, 166.4, 154.0, 146.2, 137.5, 134.7, 133.7, 131.8, 131.0,
128.5, 128.2, 127.2, 120.8, 118.8, 114.1, 106.4, 66.7, 66.2, 57.6,
53.9; HRMS (ESI) m/z calcd for C27H N O S, 488.1882; found:
28 4 3
H
28
N
4
O
3
found: 489.1950 [M+H]+.
489.1950 [M+H]+.
4
.2.1.8.
4-Fluoro-N-(3-((6-(2-morpholin-4-yl-
ethoxy)benzothiazol-2-ylamino)methyl)phenyl)benzamide (14c)
4.2.1.13. 3-Chloro-N-(4-((6-(2-morpholin-4-yl-
ethoxy)benzothiazol-2-ylamino)methyl)phenyl)benzamide (14h)
A mixture of 13b and 4-fluorobenzoyl chloride in MeCN
A mixture of 13c and 3-chlorobenzoyl chloride in MeCN
1
1
afforded 14c (14% yield): H NMR (400 MHz, CDCl
3
) δ 8.20
afforded 14h (14% yield): H NMR (400 MHz, CDCl
3
) δ 7.85
(
1H, br s), 7.81 (2H, dd, J = 5.2, 8.4 Hz), 7.61 (1H, s), 7.56 (1H,
(1H, t, J = 1.2 Hz), 7.81 (1H, br s), 7.74 (1H, d, J = 7.6 Hz), 7.62
(2H, d, J =8.4 Hz), 7.53 (1H, dd, J = 1.2, 8.0 Hz), 7.45 (1H, d, J
= 8.8 Hz), 7.44 (1H, dd, J = 7.6, 8.0 Hz), 7.40 (2H, d, J = 8.4
Hz), 7.14 (1H, d, J = 2.4 Hz), 6.91 (1H, dd, J = 2.4, 8.8 Hz), 5.47
(1H, br s), 4.61 (2H, s), 4.12 (2H, t, J = 5.6 Hz), 3.74 (4H, t, J =
d, J = 8.0 Hz), 7.32 (1H, d, J = 8.8 Hz), 7.28 (1H, dd, J = 7.6, 8.0
Hz), 7.11-7.05 (4H, m), 6.84 (1H, dd, J = 2.4, 8.8 Hz), 4.53 (2H,
s), 4.07 (2H, t, J = 5.6 Hz), 3.72 (4H, t, J = 4.4 Hz), 2.78 (2H, t, J
=
C
5.6 Hz), 2.57 (4H, t, J = 4.4 Hz); HRMS (ESI) m/z calcd for
S, 506.1788; found: 507.1849 [M+H]+.
1
3
27
H
27FN
4
O
3
4.4 Hz), 2.80 (2H, t, J = 5.6 Hz), 2.58 (4H, t, J = 4.4 Hz);
NMR (100 MHz, CDCl + CD OD) δ 166.5, 165.4, 154.0, 146.1,
37.3, 136.5, 134.5, 133.9, 131.6, 130.8, 129.8, 128.1, 127.5,
25.5, 121.0, 118.6, 114.0, 106.3, 66.5, 66.1, 57.5, 53.8; HRMS
C
3
3
4.2.1.9.
3-Chloro-N-(3-((6-(2-morpholin-4-yl-
ethoxy)benzothiazol-2-ylamino)methyl)phenyl)benzamide (14d)
1
1
A mixture of 13b and 3-chlorobenzoyl chloride in MeCN
4 3
(ESI) m/z calcd for C27H27ClN O S, 522.1492; found: 523.1557
[M+H]+.
1
afforded 14d: H NMR (400 MHz, CDCl
3
) δ 8.03 (1H, s), 7.80
(
(
1H, t, J = 1.6 Hz), 7.68 (1H, d, J = 8.0 Hz), 7.64 (1H, s), 7.57
1H, d, J = 8.0 Hz), 7.49 (1H, td, J = 1.2, 7.6 Hz), 7.40-7.30 (4H,
4
benzothiazol-2-ylamino)methyl)phenyl)benzamide (14i)
.2.1.14.
4-Chloro-N-(4-((6-(2-morpholin-4-yl-ethoxy)-
m), 7.15 (1H, d, J = 7.6 Hz), 7.10 (1H, d, J = 2.4 Hz), 6.87 (1H,
dd, J = 2.4, 8.8 Hz), 5.97 (1H, br s), 4.59 (2H, s), 4.09 (2H, t, J =
5
A mixture of 13c and 4-chlorobenzoyl chloride in MeCN
1
.6 Hz), 3.73 (4H, t, J = 4.4 Hz), 2.79 (2H, t, J = 5.6 Hz), 2.57
afforded 14i (39% yield): H NMR (400 MHz, CDCl
3
) δ 7.96
13
(
4H, t, J = 4.4 Hz); C NMR (100 MHz, CDCl
3
+ CD
3
OD) δ
(1H, s), 7.79 (2H, d, J = 8.8 Hz), 7.58 (2H, d, J = 8.4 Hz), 7.43
(2H, d, J = 8.8 Hz), 7.41 (1H, d, J = 8.8 Hz), 7.35 (2H, d, J = 8.4
Hz), 7.13 (1H, d, J = 2.4 Hz), 6.90 (1H, dd, J = 2.4, 8.8 Hz), 5.85
(1H, br s), 4.58 (2H, s), 4.11 (2H, t, J = 5.6 Hz), 3.73 (4H, t, J =
1
1
6
54.0, 146.0, 138.5, 138.2, 136.4, 134.4, 131.6, 129.7, 129.1,
27.5, 126.4, 125.5, 123.8, 120.1, 119.9, 118.5, 113.9, 106.3,
6.5, 66.0, 57.5, 53.7; HRMS (ESI) m/z calcd for
1
3
C
27
H
27ClN
4
O
3
S, 522.1492; found: 523.1558 [M+H]+.
4.4 Hz), 2.80 (2H, t, J = 5.6 Hz), 2.58 (4H, t, J = 4.4 Hz) );
NMR (100 MHz, CDCl + CD OD) δ 166.5, 165.7, 154.0, 146.1,
37.8, 137.4, 133.8, 133.1, 130.8, 128.8, 128.6, 128.1, 121.0,
18.6, 114.0, 106.3, 66.5, 66.1, 57.5, 53.8; HRMS (ESI) m/z
C
3
3
4.2.1.10. 4-Chloro-N-(3-((6-(2-morpholin-4-yl-
1
1
ethoxy)benzothiazol-2-ylamino)methyl)phenyl)benzamide (14e)
A mixture of 13b and 4-chlorobenzoyl chloride in MeCN
calcd for C27
H
27ClN
4
O
3
S, 522.1492; found: 523.1559 [M+H]+.
1
afforded 14e (26% yield): H NMR (400 MHz, CDCl
3
) δ 8.33
4
ylethoxy)benzothiazol-2-ylamino)methyl)phenyl)benzamide (14j)
.2.1.15.
4-Methoxy-N-(4-((6-(2-morpholin-4-
(
8
1H, br s), 7.72 (2H, d, J = 8.4 Hz), 7.61 (1H, s), 7.56 (1H, d, J =
.4 Hz), 7.34 (2H, d, J = 8.4 Hz), 7.30-7.25 (2H, m), 7.09 (1H, d,
J = 7.6 Hz), 7.06 (1H, d, J = 2.4 Hz), 6.83 (1H, dd, J = 2.4, 8.8
Hz), 4.52 (2H, s), 4.07 (2H, t, J = 5.6 Hz), 3.72 (4H, t, J = 4.4
Hz), 2.78 (2H, t, J = 5.6 Hz), 2.57 (4H, t, J = 4.4 Hz); HRMS
A mixture of 13c and 4-methoxybenzoyl chloride in MeCN
1
afforded 14j: H NMR (400 MHz, CDCl
3
) δ 7.94 (1H, br s), 7.83
(2H, d, J = 8.4 Hz), 7.58 (2H, d, J = 8.4 Hz), 7.40 (1H, d, J = 8.8
Hz), 7.32 (2H, d, J = 8.4 Hz), 7.13 (1H, d, J = 2.4 Hz), 6.94 (2H,
d, J = 8.4 Hz), 6.89 (1H, dd, J = 2.4, 8.8 Hz), 5.94 (1H, br s),
(
[
4 3
ESI) m/z calcd for C27H27ClN O S, 522.1492; found: 523.1559
M+H]+.
4
=
.56 (2H, s), 4.10 (2H, t, J = 5.6 Hz), 3.86 (3H, s), 3.73 (4H, t, J
4.4 Hz), 2.79 (2H, t, J = 5.6 Hz), 2.57 (4H, t, J = 4.4 Hz);
4
.2.1.11. N-(3-((6-(2-Morpholin-4-yl-ethoxy)benzothiazol-2-
ylamino)methyl)phenyl)-4-nitrobenzamide (14f)
30 4 4
HRMS (ESI) m/z calcd for C28H N O S, 518.1988; found:
A mixture of 13b and 4-nitrobenzoyl chloride in MeCN
519.2053 [M+H]+.
1
afforded 14f: H NMR (400 MHz, CDCl
3
) δ 8.28 (2H, d, J = 8.8
4.2.1.16. N-(4-((6-(2-Morpholin-4-ylethoxy)benzothiazol-2-
ylamino)methyl)phenyl)benzenesulfonamide (14k)
Hz), 8.12 (1H, br s), 7.99 (2H, d, J = 8.8 Hz), 7.65 (1H, s), 7.61
1H, d, J = 8.0 Hz), 7.39 (1H, d, J = 8.8 Hz), 7.36 (1H, dd, J =
(
7
6
.6, 8.0 Hz), 7.18 (1H, d, J = 7.6 Hz), 7.10 (1H, d, J = 2.4 Hz),
.88 (1H, dd, J = 2.4, 8.8 Hz), 4.61 (2H, s), 4.10 (2H, t, J = 5.6
A mixture of 13c and phenyl sulfonyl chloride in MeCN
1
afforded 14k: H NMR (400 MHz, CDCl
3
) δ 7.76 (2H, d, J = 8.4
Hz), 3.74 (4H, t, J = 4.4 Hz), 2.80 (2H, t, J = 5.6 Hz), 2.59 (4H, t,
J = 4.4 Hz); HRMS (ESI) m/z calcd for C27H N O S, 533.1733;
27 5 5
found: 534.1799 [M+H]+.
Hz), 7.50 (1H, t, J = 7.6 Hz), 7.40 (2H, dd, J = 7.6, 8.4 Hz), 7.32
(1H, d, J = 8.8 Hz), 7.22 (2H, d, J = 8.4 Hz), 7.11 (1H, d, J = 2.4
Hz), 7.03 (2H, d, J = 8.4 Hz), 6.86 (1H, dd, J = 2.4, 8.8 Hz), 4.49
(
(
2H, s), 4.10 (2H, t, J = 5.6 Hz), 3.73 (4H, t, J = 4.4 Hz), 2.80
2H, t, J = 5.6 Hz), 2.58 (4H, t, J = 4.4 Hz); C NMR (100 MHz,
4
.2.1.12. N-(4-((6-(2-Morpholin-4-yl-ethoxy)benzothiazol-2-
13
ylamino)methyl)phenyl)benzamide (14g)
CDCl
3
) δ 166.0, 154.3, 146.3, 139.1, 136.1, 134.6, 133.0, 131.2,
1
29.0, 128.6, 127.1, 121.9, 119.2, 114.3, 106.5, 66.9, 66.5, 57.7,