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MedChemComm
Page 8 of 14
DOI: 10.1039/C8MD00056E
ARTICLE
Journal Name
1
3
-1
7
.87 (t, 1H, J=8.0 Hz, H4´´), 7.35–7.28 (m, 1H, H5´´). C NMR 55.8, 55.8. IR (ATR-Ge, cm ): 3380, 3095, 1693 (C=O, CONH),
125 MHz, Pyridine-d ) δ 163.1, 158.9, 153.3, 151.0, 150.0, 1535, 1499, 1266, 1132, 1019, 953, 907, 873, 816, 740, 704.
48.4, 145.4, 144.4, 143.5, 137.2, 123.0, 120.9, 113.1. IR (ATR- Anal. calcd. for C16 S (MW 376.82): C, 51; H, 3.48; N,
(
5
1
4 3
H13ClN O
-1
Ge, cm ): 3153, 3073, 3007, 1677 (C=O, CONH), 1551, 1295, 14.87. Found: C, 50.94; H, 3.59; N, 14.44.
020, 903, 743, 706. Anal. calcd. for C13 OS (MW 283.31): 5-Chloro-N-(4-(pyridin-2-yl)thiazol-2-yl)pyrazine-2-
C, 55.11; H, 3.2; N, 24.72. Found: C, 54.78; H, 3.16; N, 24.46. carboxamide (8f). Off-white solid. Yield: 66%. mp 244.3–245.3
-Chloro-N-(4-phenylthiazol-2-yl)pyrazine-2-carboxamide (8a). °C. H NMR (500 MHz, DMSO-d
1
9 5
H N
1
5
6
, 55 °C) δ 12.34 (bs, 1H, NH),
Pale yellow solid. Yield: 24%. mp 187.3–189.4 °C. H NMR (500 9.16 (s, 1H, H3), 8.92 (s, 1H, H6), 8.60 (d, 1H, J=4.4 Hz, H6´´),
MHz, DMSO-d , 55 °C) δ 12.37 (bs, 1H, NH), 9.14 (s, 1H, H3), 8.02 (d, 1H, J=7.8 Hz, H3´´), 7.91–7.84 (m, 2H, H5´, H4´´), 7.34–
.94 (s, 1H, H6), 7.94 (d, 2H, J=7.4 Hz, H2´´, H6´´), 7.72 (s, 1H, 7.28 (m, 1H, H5´´). C NMR (125 MHz, Pyridine-d
H5´), 7.43 (t, 2H, J=7.4 Hz, H3´´. H5´´), 7.36–7.30 (m, 1H, H4´´). 158.9, 153.3, 152.6, 151.1, 150.0, 145.1, 143.6, 142.9, 137.2,
1
6
1
3
8
5
) δ 162.4,
1
3
-1
C NMR (125 MHz, Pyridine-d
5
) δ 162.3, 158.7, 152.6, 150.8, 123.0, 120.9, 113.2. IR (ATR-Ge, cm ): 3356, 3113, 1689 (C=O,
1
45.1, 143.6, 142.9, 135.7, 129.2, 128.3, 126.6, 109.2. IR (ATR- CONH), 1548, 1128, 1021, 922, 898, 803, 745, 703. Anal. calcd.
-1
Ge, cm ): 3358, 3348, 2926, 1688 (C=O, CONH), 1537, 1129, for C13
023, 898, 741, 692. Anal. calcd. for C14 ClN OS (MW 316.76): Found: C, 49.47; H, 2.44; N, 21.95.
C, 53.09; H, 2.86; N, 17.69. Found: C, 53.24; H, 2.95; N, 17.17.
-Chloro-N-(4-(4-fluorophenyl)thiazol-2-yl)pyrazine-2-
8 5
H ClN OS (MW 317.75): C, 49.14; H, 2.54; N, 22.04.
1
H
9
4
6-Chloro-N-(4-phenylthiazol-2-yl)pyrazine-2-carboxamide (9a).
1
5
Yellow solid. Yield: 43%. mp 206.8–213.5 °C. H NMR (500
carboxamide (8b). Pale yellow solid. Yield: 16%. mp 197.4– MHz, DMSO-d
6
, 55 °C) δ 12.51 (bs, 1H, NH), 9.26 (s, 1H, H3),
) δ 12.63 (bs, 1H, NH), 9.13 9.05 (s, 1H, H5), 7.95 (d, 2H, J=7.6 Hz, H2´´, H6´´), 7.73 (s, 1H,
d, J=1.0 Hz, 1H, H3), 8.96 (d, J=1.0 Hz, 1H, H6), 8.01–7.93 (m, H5´), 7.44 (t, 2H, J=7.6 Hz, H3´´. H5´´), 7.36–7.31 (m, 1H, H4´´).
1
198 °C. H NMR (500 MHz, DMSO-d
6
(
1
3
2
1
H, H2´´, H6´´), 7.74 (s, 1H, H5´), 7.29–7.23 (m, 2H, H3´´, H5´´).
C NMR (125 MHz, Pyridine-d
5
) δ 162.0, 158.7, 150.8, 148.4,
3
C NMR (125 MHz, DMSO-d ) δ 162.0 (d, J=245.1 Hz), 161.7, 148.1, 144.3, 143.3, 135.3, 129.2, 128.3, 126.6, 109.3. IR (ATR-
57.5, 151.6, 148.5, 144.5, 143.7, 142.7, 130.9, 128.0 (d, J=8.5 Ge, cm ): 3113, 3060, 1682 (C=O, CONH), 1550, 1296, 1170,
6
-1
1
-1
Hz), 115.8 (d, J=21.0 Hz), 109.2. IR (ATR-Ge, cm ): 3371, 3362, 1010, 938, 904, 802, 765, 716. Anal. calcd. for C14
H
9
ClN
101, 1682 (C=O, CONH), 1541, 1132, 1024, 898, 846, 756, (MW 316.76): C, 53.09; H, 2.86; N, 17.69. Found: C, 52.71; H,
06. Anal. calcd. for C14 ClFN OS (MW 334.75): C, 50.23; H, 2.84; N, 17.48.
4
OS
3
7
2
5
H
8
4
.41; N, 16.74. Found: C, 50.09; H, 2.39; N, 16.66.
6-Chloro-N-(4-(4-fluorophenyl)thiazol-2-yl)pyrazine-2-
carboxamide (9b). Yellow-orange solid. Yield: 68%. mp 222.9–
-Chloro-N-(4-(4-chlorophenyl)thiazol-2-yl)pyrazine-2-
1
carboxamide (8c). Pale yellow solid. Yield: 33%. mp 219–220.1 224.8 °C. H NMR (500 MHz, DMSO-d
6
) δ 12.74 (bs, 1H, NH),
1
°
C. H NMR (300 MHz, DMSO-d
H, H3), 8.97 (s, 1H, H6), 8.01–7.90 (m, 2H, AA´, BB´, H2´´, 7.85 (s, 1H, H5´), 7.32–7.21 (m, 2H, H3´´, H5´´). C NMR (125
H6´´), 7.83 (s, 1H, H5´), 7.54–7.44 (m, 2H, AA´, BB´, H3´´, H5´´). MHz, DMSO-d ) δ 162.1 (d, J=245.1 Hz), 161.4, 157.5, 148.5,
) δ 162.1, 157.9, 151.9, 148.6, 148.2, 147.4, 143.8, 142.7, 130.9, 128.0 (d, J=7.5 Hz), 115.8 (d,
6
) δ 12.70 (bs, 1H, NH), 9.14 (s, 9.26 (s, 1H, H3), 9.07 (s, 1H, H5), 8.04–7.92 (m, 2H, H2´´, H6´´),
1
3
1
6
1
3
C NMR (75 MHz, DMSO-d
44.8, 144.1, 143.0, 133.4, 132.9, 129.2, 128.0, 110.4. IR (ATR- J=22.0 Hz), 109.2. IR (ATR-Ge, cm ): 3119, 3060, 2925, 1682
6
-1
1
-1
Ge, cm ): 3373, 3353, 3093, 1678 (C=O, CONH), 1540, 1132, (C=O, CONH), 1553, 1486, 1301, 1171, 1011, 937, 906, 834,
1
3
1
5
017, 897, 840, 751, 703. Anal. calcd. for C14
8 2 4 8 4
H Cl N OS (MW 797, 739, 706. Anal. calcd. for C14H ClFN OS (MW 334.75): C,
51.21): C, 47.88; H, 2.3; N, 15.95. Found: C, 48.17; H, 2.25; N, 50.23; H, 2.41; N, 16.74. Found: C, 50.48; H, 2.45; N, 16.7.
5.98.
6-Chloro-N-(4-(4-chlorophenyl)thiazol-2-yl)pyrazine-2-
-Chloro-N-(4-(4-methoxyphenyl)thiazol-2-yl)pyrazine-2-
carboxamide (9c). Yellow solid. Yield: 27%. mp 228.3–230.2 °C.
1
H NMR (500 MHz, DMSO-d ) δ 12.81 (bs, 1H, NH), 9.27 (s, 1H,
6
carboxamide (8d). Pale yellow solid. Yield: 32%. mp 221.4–
1
23.2 °C. H NMR (500 MHz, DMSO-d
2
6
, 65 °C) δ 12.22 (bs, 1H, H3), 9.08 (s, 1H, H5), 8.00–7.94 (m, 2H, AA´, BB´, H2´´, H6´´),
1
3
NH), 9.13 (s, 1H, H3), 8.92 (s, 1H, H6), 7.89–7.81 (m, AA´, BB´, 7.84 (s, 1H, H5´), 7.53–7.48 (m, 2H, AA´, BB´, H3´´, H5´´).
C
2
6
H, H2´´, H6´´), 7.53 (s, 1H, H5´), 7.02–6.95 (m, AA´, BB´, 2H, NMR (125 MHz, DMSO-d ) δ 161.5, 157.6, 148.3, 148.2, 147.4,
13
). C NMR (125 MHz, Pyridine-d
-
H3´´, H5´´), 3.80 (s, 3H, OCH
3
5
)
143.8, 142.8, 133.1, 132.6, 129.0, 127.7, 110.2. IR (ATR-Ge, cm
1
): 3059, 1681 (C=O, CONH), 1547, 1298, 1091, 1011, 937, 904,
δ 162.2, 160.1, 158.6, 152.5, 150.7, 145.1, 143.6, 142.9, 128.2,
-1
1
1
7
3
5
27.9, 114.6, 107.3, 55.3. IR (ATR-Ge, cm ): 3395, 3369, 3102, 831, 734, 710. Anal. calcd. for C14
685 (C=O, CONH), 1541, 1253, 1130, 1020, 899, 840, 758, 47.88; H, 2.3; N, 15.95. Found: C, 47.89; H, 2.25; N, 15.85.
03. Anal. calcd. for C15 S (MW 346.79): C, 51.95; H, 6-Chloro-N-(4-(4-methoxyphenyl)thiazol-2-yl)pyrazine-2-
8 2 4
H Cl N OS (MW 351.21): C,
4 2
H11ClN O
.2; N, 16.16. Found: C, 51.58; H, 3.22; N, 15.94.
carboxamide (9d). Yellow-orange solid. Yield: 37%. mp 237.1–
1
238.4 °C. H NMR (500 MHz, Pyridine-d ) δ 9.61 (s, 1H, H3),
5
-Chloro-N-(4-(3,4-dimethoxyphenyl)thiazol-2-yl)pyrazine-2-
carboxamide (8e). Yellow solid. Yield: 27%. mp 210.7–212.4 °C. 9.00 (s, 1H, H5), 8.23–8.19 (m, 2H, AA´, BB´, H2´´, H6´´), 7.60 (s,
1
H NMR (500 MHz, Pyridine-d
H, J=1.2 Hz, H3), 8.84 (d, 1H, J=1.2 Hz, H6), 7.82 (d, 1H, J=1.8 OCH
Hz, H2´´), 7.78 (dd, 1H, J=8.6 Hz, J=1.8 Hz, H6´´), 7.58 (s, 1H, 150.8, 148.4, 148.1, 144.4, 143.3, 128.2, 127.9, 114.6, 107.4,
5
) δ 14.33 (bs, 1H, NH), 9.37 (d, 1H, H5´), 7.21–7.15 (m, 2H, AA´, BB´, H3´´, H5´´), 3.79 (s, 3H,
1
3
1
3 5
). C NMR (125 MHz, Pyridine-d ) δ 161.9, 160.1, 158.6,
-1
H5´), 7.06 (d, 1H, J=8.6 Hz, H5´´), 3.84 (s, 3H, OCH
1
OCH ). C NMR (125 MHz, Pyridine-d ) δ 162.2, 158.5, 152.5, 1488, 1294, 1248, 1174, 1032, 1009, 938, 905, 826, 787, 741,
3 5
3
), 3.79 (s, 3H, 55.3. IR (ATR-Ge, cm ): 3110, 3058, 1681 (C=O, CONH), 1547,
3
150.8, 145.0, 143.5, 142.9, 128.5, 119.1, 112.5, 110.7, 107.5,
8
| J. Name., 2012, 00, 1-3
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