Med Chem Res
7.96 (1H, dd, 3JH–H 8.9 Hz, 4JF–H 5.0 Hz, H-4), 7.90 (2 H, d,
8.6 Hz, NH-H-15), 7.96 (3H, m, H-4, H-7, H-18), 7.87 (1H,
3
3
3
3JH–H 7.6 Hz, H-17, H-22), 7.54 (1H, t, JH–H 7.6 Hz, H-
d, JH–H 7.6 Hz, H-20), 7.61 (1H, d, JH–H 7.6 Hz, H-22),
7.51 (1H, t, 3JH–H 7.6 Hz, H-21), 7.36 (1H, dt, 4JH–H 2.4 Hz,
3JH–H 9.0 Hz, 3JF–C 9.0 Hz, H-5), 5.31 (1H, quin, 3JH–H 7.2
Hz, H-1), 4.38 (1H, t, 3JH–H 8.6 Hz, H-12), 2.17 (1H, m, H-
13), 1.58 (3H, d,3JH–H 7.2 Hz, H-2), 0.97 (6H, d, 3JH–H 6.5
Hz, H-14); 13C NMR (100.62 MHz, DMSO-d6): δC 175.4
(d, 4JF–C 3.3 Hz, C-9), 171.1 (C-11), 165.2 (C-16), 159.5 (d,
1JF–C 242.4 Hz, C-6), 149.6 (C-3), 136.2 (C-17), 135.9 (d,
3JF–C 11.8 Hz, C-8), 133.1 (C-19), 131.1 (C-20), 130.2 (C-
3
20), 7.47 (2H, t, JH–H 7.6 Hz, H-19, H-21), 7.36 (1H, dt,
3
3
4JH–H 2.7 Hz, JH–H 9.1 Hz, JF–H 9.1 Hz, H-5), 5.31 (1H,
3
3
quin, JH–H 7.2 Hz, H-1), 4.40 (1H, t, JH–H 8.6 Hz, H-12),
3
2.17 (1H, m, H-13), 1.58 (3H, d, JH–H 7.2 Hz, H-2), 0.97
(6H, d,3JH–H 6.7 Hz, H-14); 13C NMR (100.62 MHz,
4
DMSO-d6): δC 175.5 (d, JF–C 3.2 Hz, C-9), 171.3 (C-11),
166.5 (C-16), 159.5 (d, JF–C 241.8 Hz, C-6), 149.6 (C-3),
1
3
135.9 (d, JF–C 11.6 Hz, C-8), 134.3 (C-17), 131.3 (C-20),
128.2 (C-19, C-21), 127.6 (C-18, C-22), 123.7 (d, 3JF–C 9.6
21), 127.4 (C-22), 126.4 (C-18), 123.7 (d, JF–C 9.7 Hz, C-
3
2
2
2
2
Hz, C-4), 114.5 (d, JF–C 24.8 Hz, C-5), 108.6 (d, JF–C
26.9 Hz, C-7), 59.1 (C-12), 47.3 (C-1), 30.2 (C-13), 20.2
(C-2), 19.4 (C-14), 19.0 (C-14); 19F NMR (376,46 MHz,
DMSO-d6): δF −116.5. Anal. calcd. for C21H22FN3O2S
(399.48): C, 63.14; H, 5.55; N, 10.52; S, 8.03%. Found C,
64.08; H, 5.48; N, 10.60; S, 8.12%. HR-MS: for C21H22FN3
O2S [M + H+] calcd. 400.14895 m/z, found 400.14915 m/z.
4), 114.5 (d, JF–C 24.8 Hz, C-5), 108.6 (d, JF–C 27.1 Hz,
C-7), 59.3 (C-12), 47.3 (C-1), 30.1 (C-13), 20.1 (C-2), 19.3
(C-14), 19.1 (C-14); 19F NMR (376.46 MHz, DMSO-d6): δF
−116.5. Anal. calcd. for C21H21ClFN3O2S (433.93): C,
58.13; H, 4.88; N, 9.68; S, 7.39%. Found C, 58.08; H, 4.78;
N, 9.79; S, 7.48%. HR-MS: for C21H21ClFN3O2S [M +
H+] calcd. 434.10998 m/z, found 434.11017 m/z.
2-chloro-N-[(1S)-1-{[(1R)-1-(6-fluoro-1,3-benzothiazol-2-
yl)ethyl]carbamoyl}-2-methylpropyl]-benzamide (11b)
4-chloro-N-[(1S)-1-{[(1R)-1-(6-fluoro-1,3-benzothiazol-2-
yl)ethyl]carbamoyl}-2-methylpropyl]- benzamide (11d)
White solid; yield 85.0%, m.p. 223–224 (from toluene); IR
(νmax, cm−1): 3255, 1544 (NH of CONH), 1631 (CO of
White solid; yield 82.0%; m.p. 226–227 °C (from toluene); IR
(νmax, cm−1): 3270, 1539 (NH of CONH), 1635 (CO of
CONH), 1458 (C=N); 1H NMR (400.13 MHz, DMSO-d6): δH
9.03 (1H, d, 3JH–H 7.7 Hz, NH-H-10), 8.48 (1H, d, 3JH–H 8.6
Hz, NH-H-15), 7.97–7.92 (4H, m, H-4, H-7, H-19, H-21),
1
CONH), 1451 (C=N); H NMR (400.13 MHz, DMSO-d6):
δH 9.03 (1H, d, 3JH–H 7.9 Hz, NH-H-10), 8.65 (1H, d, 3JH–H
4
3
9.0 Hz, NH-H-15), 8.00 (1H, dd, JH–H 2.3 Hz, JF–H 8.6
3
4
3
4
Hz, H-7), 7.96 (1H, dd, JH–H 8.8 Hz, JF–H 4.7 Hz, H-4),
7.49–7.39 (4H, m, H-19, H-20, H-21, H-22), 7.36 (1H, dt,
7.53 (2H, d, JH–H 8.6 Hz, H-18, H-22), 7.35 (1H,dt, JH–H
3
3
2.7 Hz, JH–H 9.2 Hz, JF–H 9.2 Hz, H-5), 5.31 (1H, quin,
4JH–H 2.5 Hz, JH–H 9.0 Hz, JF–C 9.0 Hz, H-5), 5.32 (1H,
3JH–H 7.2 Hz, H-1), 4.39 (1H, t, JH–H 8.6 Hz, H-12), 2.17
3
3
3
3
3
quin, JH–H 7.2 Hz, H-1), 4.38 (1H, t, JH–H 8.4 Hz, H-12),
(1H, m, H-13), 1.58 (3H, d,3JH–H 7.1 Hz, H-2), 0.97 (6H,
d,3JH–H 6.7 Hz, H-14); 13C NMR (100,62 MHz, DMSO-d6):
δC 175.4 (d, 4JF–C 3.0 Hz, C-9), 171.2 (C-11), 165.6 (C-16),
3
2.11 (1H, m, H-13), 1.59 (3H, d, JH–H 7.1Hz, H-2), 0.98
(6H, d,3JH–H 6.8 Hz, H-14); 13C NMR (100.62 MHz,
4
1
DMSO-d6): δC 175.5 (d, JF–C 3.0 Hz, C-9), 170.8 (C-11),
159.5 (d, JF–C 242.0 Hz, C-6), 149.6 (C-3), 136.1 (C-20),
135.9 (d, JF–C 11.8 Hz, C-8), 133.0 (C-17), 129.6 (C-18,
C22), 128.3 (C-19, C-21), 123.7 (d, JF–C 9.7 Hz, C-4),
168.4 (C-16), 159.5 (d, 1JF–C 242.3 Hz C-6), 149.6 (d, 5JF–C
3
3
3
1.5 Hz, C-3), 136.8 (C-18), 135.9 (d, JF–C 11.7 Hz, C-8),
130.7 (C-17), 129.9 (C-20), 129.5 (C-19), 129.1 (C-22),
114.5 (d, 2JF–C 24.9 Hz, C-5), 108.6 (d, 2JF–C 27.1 Hz, C-7),
59.2 (C-12), 47.3 (C-1), 30.1 (C-13), 20.1 (C-2), 19.3 (C-
14), 19.0 (C-14); 19F NMR (376.46 MHz, DMSO-d6): δF
-116.5. Anal. calcd. for C21H21ClFN3O2S (433.93): C,
58.13; H, 4.88; N, 9.68; S, 7.39%. Found C, 58.06; H, 4.75;
N, 9.77; S, 7.51%. HR-MS: for C21H21ClFN3O2S [M +
H+] calcd. 434.10998 m/z, found 434.11020 m/z.
3
2
127.0 (C-21), 123.7 (d, JF–C 9.5 Hz, C-4), 114.6 (d, JF–C
2
24.7 Hz, C-5), 108.6 (d, JF–C 27.1 Hz, C-7), 58.9 (C-12),
47.3 (C-1), 30.3 (C-13), 20.1 (C-2), 19.4 (C-14), 18.7 (C-
14); 19F NMR (376,46 MHz, DMSO-d6): δF −116.5; Anal.
calcd. for C21H21ClFN3O2S (433.93): C, 58.13; H, 4.88; N,
9.68; S, 7.39%. Found C, 58.33; H, 5.00; N, 9.46; S, 7.19%.
HR-MS: for C21H21ClFN3O2S [M + H+] calcd. 434.10998
m/z, found 434.11011 m/z.
3-fluoro-N-[(1S)-1-{[(1R)-1-(6-fluoro-1,3-benzothiazol-2-
yl)ethyl]carbamoyl}-2-methylpropyl]-benzamide (11e)
3-chloro-N-[(1S)-1-{[(1R)-1-(6-fluoro-1,3-benzothiazol-2-
yl)ethyl]carbamoyl}-2-methylpropyl]-benzamide (11c)
White solid; yield 85.0%; m.p. 195–196 °C (from toluene);
IR (νmax, cm−1): 3278, 1540 (NH of CONH), 1634 (CO of
1
White solid; yield 84.0%; m.p. 213–214 °C (from toluene);
IR (νmax, cm−1): 3252, 1533 (NH of CONH), 1629 (CO of
CONH), 1458 (C=N); H NMR (400.13 MHz, DMSO-d6):
δH 9.05 (1H, d, 3JH–H 7.8 Hz, NH-H-10), 8.53 (1H, d, 3JH–H
1
CONH), 1457 (C=N); H NMR (400.13 MHz, DMSO-d6):
8.7 Hz, NH-H-15), 7.96 (2H, m, H-4, H-7), 7.76 (2H, m, H-
δH 9.02 (1H, d, 3JH–H 7.6 Hz, NH-H-10), 8.55 (1H, d, 3JH–H
18, H-22), 7.52 (1H, m, H-21), 7.39 (1H, dt, JH–H 2.4 Hz,
4